1,3-Diisopropyl-2-thiourea | Aliphatic Chain Hydrocarbons

CAS No. :	2986-17-6
Formula :	C₇H₁₆N₂S
M.W :	160.28
SMILES Code :	S=C(NC(C)C)NC(C)C
MDL No. :	MFCD00040485
InChI Key :	KREOCUNMMFZOOS-UHFFFAOYSA-N
Pubchem ID :	2758386

Safety of [ 2986-17-6 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H302
Precautionary Statements:	P301+P312+P330

Computational Chemistry of [ 2986-17-6 ] Show Less

Physicochemical Properties

Num. heavy atoms	10
Num. arom. heavy atoms	0
Fraction Csp3	0.86
Num. rotatable bonds	4
Num. H-bond acceptors	0.0
Num. H-bond donors	2.0
Molar Refractivity	49.16
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	56.15 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.37
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	1.57
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	1.27
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	1.22
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	1.6
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	1.61

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-1.56
Solubility	4.43 mg/ml ; 0.0276 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Very soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-2.36
Solubility	0.7 mg/ml ; 0.00437 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-1.77
Solubility	2.72 mg/ml ; 0.017 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	No
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	No
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	No
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	No
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-6.16 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	1.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	1.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.81

Application In Synthesis of [ 2986-17-6 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2986-17-6 ]

[ 2986-17-6 ] Synthesis Path-Downstream 1~54

1
[ 5694-65-5 ]
[ 2986-17-6 ]
S-(2-dicyanacetoxy-ethyl)-N,N'-diisopropyl-isothiourea [ No CAS ]

References: [1]Journal of the American Chemical Society,1958,vol. 80,p. 2788,2793.

2
[ 79-03-8 ]
[ 2986-17-6 ]
[ 99849-69-1 ]

References: [1]Patent: US2822412,1954, .

3
[ 75-15-0 ]
[ 75-31-0 ]
[ 2986-17-6 ]

Yield	Reaction Conditions	Operation in experiment
97%	In water; at 20℃; for 0.166667h;Green chemistry;	General procedure: To a 50 mL round bottom flask equipped with a magnetic stirrer, add carbon disulphide (5 mmol) andamine (10 mmol) in ice cold condition followed by addition of water (5 mL). Cork the flask. Thereaction mixture was stirred vigorously at room temperature. The progress of the reaction was checkedby TLC (10percent MeOH: chloroform or EtOAc: hexane). After completion of reaction, solid was obtainedby removal of water under reduced pressure on rotary evaporator while in some cases (Entry 7, 9, 10,11 and 14, 15) the reaction mixture solidified when the reaction on completion. The obtained solidproduct was recrystallized with ethanol or washing with mixture EtOAc: hexane.
97%	In water; at 20℃; for 0.166667h;Green chemistry;	General procedure: To a 50 mL round bottom flask equipped with a magnetic stirrer, add carbon disulphide (5 mmol) and amine (10 mmol) in ice cold condition followed by addition of water (5 mL). Cork the flask. The reaction mixture was stirred vigorously at room temperature. The progress of the reaction was checked by TLC (10percent MeOH: chloroform or EtOAc: hexane). After completion of reaction, solid was obtained by removal of water under reduced pressure on rotary evaporator while in some cases (Entry 7, 9, 10, 11 and 14, 15) the reaction mixture solidified when the reaction on completion. The obtained solid product was recrystallized with ethanol or washing with mixture EtOAc : hexane.
	In toluene; at 35℃; for 1.0h;Large scale;	The first 140 kg isopropylamine and 400 kg toluene into reactor and, start the stirring, dropping 70 kg carbon disulfide, temperature control in the 35 °C following, thermal insulation reaction 1 hours, at the same time for 30percent of the mass fraction of the sodium hydroxide solution to absorb the reaction produced in the process of hydrogen sulfide gas, generating sodium sulfide solution for secondary oxidation of the desulfurization reaction; cooling, filtration, and dried to obtain the N, N' - diisopropyl thiourea.

References: [1]Synthetic Communications,2015,vol. 45,p. 236 - 244.
[2]Synthetic Communications,2015,vol. 45,p. 376 - 385.
[3]Journal of Heterocyclic Chemistry,2016,vol. 53,p. 588 - 594.
[4]Patent: US2849420,1953, .
[5]Patent: CN109485583,2019,A .Location in patent: Paragraph 0037-0038; 0044; 0050.

4
[ 75-15-0 ]
[ 75-31-0 ]
[ 2253-73-8 ]
[ 2986-17-6 ]

References: [1]Monatshefte fur Chemie,1882,vol. 3,p. 172.
Chemische Berichte,1875,vol. 8,p. 805.

5
[ 2253-73-8 ]
[ 75-31-0 ]
[ 2986-17-6 ]

References: [1]Justus Liebigs Annalen der Chemie,1969,vol. 722,p. 52 - 79.

6
[ 75-36-5 ]
[ 2986-17-6 ]
[ 14041-88-4 ]

References: [1]Patent: US2822412,1954, .

7
[ 141-75-3 ]
[ 2986-17-6 ]
[ 99993-89-2 ]

References: [1]Patent: US2822412,1954, .

8
[ 628-21-7 ]
[ 2986-17-6 ]
N,N',N'',N'''-tetraisopropyl-S,S'-butanediyl-bis-isothiourea [ No CAS ]

References: [1]Journal of Organic Chemistry,1953,vol. 18,p. 728,731,733.

9
[ 629-03-8 ]
[ 2986-17-6 ]
1,6-bis-(N,N'-diisopropyl-carbamimidoylmercapto)-hexane [ No CAS ]

References: [1]Journal of the American Pharmaceutical Association (1912),1956,vol. 45,p. 423,424.

10
[ 19218-94-1 ]
[ 2986-17-6 ]
N,N'-diisopropyl-S-tetradecyl-isothiourea; hydriodide [ No CAS ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 4271.

11
[ 2986-17-6 ]
[ 108-12-3 ]
[ 100396-44-9 ]

References: [1]Patent: US2822412,1954, .

12
[ 2986-17-6 ]
[ 112-82-3 ]
S-hexadecyl-N,N'-diisopropyl-isothiourea; hydrobromide [ No CAS ]

References: [1]Journal of the American Chemical Society,1952,vol. 74,p. 4271.

13
[ 2986-17-6 ]
[ 74-88-4 ]
[ 108372-20-9 ]

References: [1]Journal of Organic Chemistry,1957,vol. 22,p. 925,931.

14
[ 2986-17-6 ]
[ 75431-03-7 ]

References: [1]Journal of Organic Chemistry,1957,vol. 22,p. 925,931.
[2]Journal of Organic Chemistry,2006,vol. 71,p. 1295 - 1305.

15
[ 2986-17-6 ]
[ 693-13-0 ]

Yield	Reaction Conditions	Operation in experiment
99%	With cyclopentadienyl iron(II) dicarbonyl dimer; In tetrahydrofuran; at 60℃; for 24.0h;Inert atmosphere;	To the reaction vessel, 0.3 mmol of the thiourea compound shown in Table 3, 0.9 mmol of [CpFe (CO) 2] 2 as in Example 1-2 as an iron compound and 9 mL of tetrahydrofuran were added and the mixture was stirred at 60 ° C. under a nitrogen atmosphere And allowed to react for 24 hours. However, only in Example 3-9, each charged amount was multiplied by 100/3 and carried out.After completion of the reaction, the resulting reaction solution was analyzed with a gas chromatograph mass spectrometer (GC-MS), and it was found that the product shown in Table 3 was produced at the yield shown in Table 3.The reaction solutions obtained in Examples 3-1 to 3-9 were cooled to room temperature, water was added, and the product was extracted with ethyl acetate. Subsequently, the organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, then filtered and concentrated to obtain a crude product, and the crude product was used in Examples 3-1 to 3-8, silica gel (Developing solvent: ethyl acetate / hexane (mixing ratio was appropriately adjusted)), and purified by distillation in Example 3-9 to obtain the respective products
93%	With sodium chlorate; N-benzyl-N,N,N-triethylammonium chloride; In water; benzene; at 55 - 70℃; for 4.0h;Large scale;	Will be 100 kg N, N ' - diisopropyl thiourea, 400 kg benzene is added to the other in a reaction kettle, plus 5 kg piece of alkali, 15 kg catalyst polyethylene glycol, the kettle temperature rises to 60 °C, dropwise 600 kg sodium hypochlorite, temperature control in the 55 - 65 °C between, reaction 2 hours, standing 20 minutes, discarding lower aqueous phase; filtering the aqueous phase after the next time for preparation of oxidizing liquid, do not discharge.The primary oxidation end of oxidizing liquid into the other in a kettle, add 2 kg catalyst, dropping 100 L sodium hypochlorite, temperature control in the 65 °C the left and the right, reaction 1 hours.Added in the reaction kettle 150 L of sodium sulfide solution, heating up to 70 °C, reaction 1 hours.Adding alkali to 5 kg, water 300 kg, stirring for half an hour, standing 20 minutes, eliminating water layer, adding 10 kg potassium carbonate drying, evaporating the solvent, pressure reducing and get the N, N' - diisopropyl carbodiimide. Yield 93percent, purity 99.5percent or more.

References: [1]Patent: JP5999596,2016,B2 .Location in patent: Paragraph 0054-0059; 0062; 0063; 0064.
[2]Patent: CN109485583,2019,A .Location in patent: Paragraph 0039-0042; 0043; 0045-0048; 0051-0054.
[3]Dalton Transactions,2013,vol. 42,p. 10271 - 10276.
[4]Synthesis,2011,p. 711 - 714.
[5]Bulletin of the Chemical Society of Japan,1980,vol. 53,p. 3658 - 3660.
[6]Justus Liebigs Annalen der Chemie,1951,vol. 571,p. 83,85.
[7]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 667 - 671.
[8]Heteroatom Chemistry,2002,vol. 13,p. 561 - 566.
[9]Patent: US2479498,1946, .

16
[ 113-00-8 ]
[ 2986-17-6 ]
1,2-Di-isopropylbiguanid [ No CAS ]

References: [1]Patent: DE2117015,1972, .
Chem.Abstr.,1973,vol. 78.

17
[ 629-03-8 ]
[ 2986-17-6 ]
2-[6-(N,N'-Diisopropyl-carbamimidoylsulfanyl)-hexyl]-1,3-diisopropyl-isothiourea [ No CAS ]

References: [1]Patent: FR1538328,1968, .
Chem.Abstr.,1969,vol. 71.

18
[ 42908-86-1 ]
[ 2986-17-6 ]
[ 57722-81-3 ]

References: [1]Chemical and Pharmaceutical Bulletin,1975,vol. 23,p. 1764 - 1774.

19
[ 4638-79-3 ]
[ 2986-17-6 ]
3-isopropyl-2-isopropylamino-4-phenyl-thiazolium; chloride [ No CAS ]

References: [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 649 - 652.

20
[ 2986-17-6 ]
[ 57508-19-7 ]
1,3-diisopropyl-1-thiazol-2-yl-thiourea [ No CAS ]

References: [1]Synthesis,1975,p. 675 - 676.

21
[ 2986-17-6 ]
[ 762-42-5 ]
[ 16238-36-1 ]

References: [1]Canadian Journal of Chemistry,1967,vol. 45,p. 939 - 951.

22
[ 2986-17-6 ]
[ 86-52-2 ]
[ 14122-41-9 ]

References: [1]Journal of Medicinal Chemistry,1967,vol. 10,p. 649 - 652.

23
[ 2986-17-6 ]
[ 92351-69-4 ]

References: [1]Chemische Berichte,1964,vol. 97,p. 1232 - 1245.

24
[ 16486-30-9 ]
[ 2986-17-6 ]

References: [1]Chemische Berichte,1967,vol. 100,p. 1602 - 1615.

25
[ 693-13-0 ]
[ 2986-17-6 ]

References: [1]Journal of Heterocyclic Chemistry,1979,vol. 16,p. 341 - 345.

26
[ 108-31-6 ]
[ 2986-17-6 ]
[ 104445-57-0 ]

References: [1]Polish Journal of Chemistry,1985,vol. 59,p. 149 - 158.

27
[ 513-86-0 ]
[ 2986-17-6 ]
1,3-diisopropyl-4,5-dimethyl-2,3-dihydro-1H-imidazol-2-thione [ No CAS ]

References: [1]Chemistry - A European Journal,2009,vol. 15,p. 9477 - 9485.
[2]Journal of the American Chemical Society,2015,vol. 137,p. 8704 - 8707.
[3]Synthesis,1993,p. 561 - 562.
[4]Chemistry - A European Journal,2018,vol. 24,p. 15026 - 15035.
[5]Chemistry - A European Journal,2012,vol. 18,p. 3621 - 3630.
[6]Organic Letters,2015,vol. 17,p. 1866 - 1869.

28
[ 534-18-9 ]
[ 75-31-0 ]
[ 2044-27-1 ]
[ 2986-17-6 ]

References: [1]Chemistry Letters,1982,p. 641 - 642.

29
[ 420-04-2 ]
[ 2986-17-6 ]
[ 76070-76-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 667 - 671.

30
[ 2986-17-6 ]
[ 4128-37-4 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 667 - 671.

31
[ 22315-46-4 ]
[ 2986-17-6 ]
2-(3,4-Dioxo-2-phenyl-cyclobut-1-enyl)-1,3-diisopropyl-isothiourea [ No CAS ]

References: [1]Liebigs Annalen der Chemie,1979,p. 1689 - 1695.

Yield	Reaction Conditions	Operation in experiment
		Representative sulfur nucleophiles to be employed in accordance with the present invention, include the following:ThioureasallylthioureaN,n'-di-n-butylthioureaN,n'-di-tert-butylthioureaN,n'-dicyclohexylthioureaN,n'-diisopropylthioureaN,n'-dimethylthioureaN-methylthioureaN,n,n',n'-tetraethylthioureaN,n,n',n'-tetramethylthiourea...

34
[ 75-31-0 ]
CS₂ [ No CAS ]
[ 2986-17-6 ]

References: [1]Chemische Berichte,1941,vol. 74,p. 1288 Anm.10.

35
[ 2986-17-6 ]
TeO₂ [ No CAS ]
cis-dibromobis(N,N'-diisopropylthiourea)tellurium(II) [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1825 - 1837.

36
[ 2986-17-6 ]
TeO₂ [ No CAS ]
trans-diiodobis(N,N'-diisopropylthiourea)tellurium(II) [ No CAS ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,2003,vol. 178,p. 1825 - 1837.

37
[ 2986-17-6 ]
[ 74-88-4 ]
N,N'-diisopropyl-S-methylisothiouronium iodide [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 1295 - 1305.

38
[ 2986-17-6 ]
1-isopropyl-5-(isopropylnitramino)-1H-tetrazole [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 1295 - 1305.

39
[ 2986-17-6 ]
1-amino-2,3-diisopropylguanidinium iodide [ No CAS ]

References: [1]Journal of Organic Chemistry,2006,vol. 71,p. 1295 - 1305.

40
[ 2986-17-6 ]
[ 151515-23-0 ]

References: [1]Synthesis,1993,p. 561 - 562.
[2]Organic Letters,2015,vol. 17,p. 1866 - 1869.

41
[ 2986-17-6 ]
[ 76070-76-3 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 667 - 671.

42
[ 2986-17-6 ]
[ 78822-77-2 ]

References: [1]Patent: US2479498,1946, .

43
[ 2986-17-6 ]
[ 16238-43-0 ]

References: [1]Canadian Journal of Chemistry,1967,vol. 45,p. 939 - 951.

44
[ 2986-17-6 ]
[ 57723-30-5 ]

References: [1]Chemical and Pharmaceutical Bulletin,1975,vol. 23,p. 1764 - 1774.
[2]Chemical and Pharmaceutical Bulletin,1975,vol. 23,p. 1764 - 1774.

45
[ 49679-45-0 ]
[ 2986-17-6 ]
[ 83778-31-8 ]

Yield	Reaction Conditions	Operation in experiment
	With acetic acid; In acetone;	EXAMPLE 14 2-[(1-Methylethylamino)(1-methylethylimino)methylthio]-3-quinoxalinecarboxylic acid ethyl ester, hydrochloride 2-Chloro-3-quinoxalinecarboxylic acid ethyl ester (4.73 g., 0.02 mole) and 3.206 g. (0.02 mole) of <strong>[2986-17-6]1,3-diisopropylthiourea</strong> were dissolved in 90 ml. of acetone and 10 ml. of acetic acid. The solution was heated on the steambath for 23/4 hours and filtered hot. The solvent in the filtrate was evaporated and the residue was triturated with ether until it solidified. Filtration gave 2.33 g. of crude product. Recrystallized from acetone-ether it afforded 1.28 g. (16.1percent) of a yellow solid, m.p. 148°-149° C. (dec). Analysis for: C18 H25 ClN4 O2 S Calculated: C, 54.47; H, 6.35; N, 14.12; Cl, 8.93; S, 8.08. Found: C, 54.44; H, 6.18; N, 14.19; Cl, 8.96; S, 8.25.

References: [1]Patent: US4349674,1982,A .

46
[ 2986-17-6 ]
[ 74-88-4 ]
[ 108372-20-9 ]

Yield	Reaction Conditions	Operation in experiment
		N,N'-diisopropylthiourea and methyl iodide are heated to yield N,N'-diisopropyl-S-methylisothiourea hydroiodide, which upon treatment with hydrazine in boiling isopropanol, yields a solution of the desired intermediate.

References: [1]Patent: US29358,1977,E1 .

47
aqueous potassium hydroxide [ No CAS ]
[ 35203-08-8 ]
[ 2986-17-6 ]
[ 503-38-8 ]
2-Isopropylimino-3-isopropyl-5-(2,6-diethylphenyl)-tetrahydro-1,3,5-thiadiazin-4-one [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
40%	In water; benzene;	STR182 A solution of 1.6 g (0.01 mole) of N-methylene-2,6-diethylaniline in 10 ml of benzene was added with stirring to 10 ml of benzene containing 1.1 g of trichloromethyl chloroformate. After 10 minutes of stirring, a solution of 1.6 g (0.01 mole) of <strong>[2986-17-6]1,3-diisopropylthiourea</strong> in 20 ml of benzene was added to the mixture and heated under reflux with stirring for one hour. The reaction mixture was admixed with 100 ml of water and shaken thoroughly. The aqueous layer was separated and mixed with 5 ml of a 30percent aqueous potassium hydroxide solution to deposit an oily substance which was extracted with benzene. The benzene layer was washed with water, dried, and concentrated to a viscous oily substance which was recrystallized from isopropanol-n-hexane (8:2) to give 1.4 g (40percent yield) of white crystals melting at 89°-90° C. NMR(CDCl3)delta: 3.50 STR183 4.50 (s. 2H: STR184 4.84 (m. 1H: STR185