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Chemical Structure| 1575-61-7 Chemical Structure| 1575-61-7

Structure of 5-Chlorovaleroyl chloride
CAS No.: 1575-61-7

Chemical Structure| 1575-61-7

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Product Details of [ 1575-61-7 ]

CAS No. :1575-61-7
Formula : C5H8Cl2O
M.W : 155.02
SMILES Code : O=C(Cl)CCCCCl
MDL No. :MFCD00000758
InChI Key :SVNNWKWHLOJLOK-UHFFFAOYSA-N
Pubchem ID :74089

Safety of [ 1575-61-7 ]

GHS Pictogram:
Signal Word:Danger
Hazard Statements:H314
Precautionary Statements:P260-P264-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P321-P363-P405-P501
Class:8
UN#:3265
Packing Group:

Application In Synthesis of [ 1575-61-7 ]

* 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 [ 1575-61-7 ]

[ 1575-61-7 ] Synthesis Path-Downstream   1~12

  • 1
  • [ 1575-61-7 ]
  • [ 98454-39-8 ]
  • [ 98454-45-6 ]
  • 2
  • [ 6281-32-9 ]
  • [ 1575-61-7 ]
  • [ 274251-01-3 ]
  • 3
  • [ 1575-61-7 ]
  • [ 23218-93-1 ]
  • [ 706791-79-9 ]
YieldReaction ConditionsOperation in experiment
100% With triethylamine; In dichloromethane; at 20℃; for 1h; 5-Chlorovaleryl chloride (2.64 g, 17 mmol, 1.1 equiv) in CH2CI2 (5 ML) was added over 2 min to a stirred solution of <strong>[23218-93-1]3-amino-5-nitro-benzoic acid methyl ester</strong> (D1) (3 g, 15.3 mmol, 1 equiv) and NEt3 (2.6 ml, 18 mmol, 1.2 equiv) in CH2CI2 (30 ML). The resulting mixture was stirred for 1 h at room temperature then washed with 2N aqueous HCI solution, dried over MGS04 and concentrated in vacuo. The residue was triturated with CH2CI2 TO give 3- (5-Chloro- pentanoylamino)-5-nitro-benzoic acid methyl ester D3 (6g, 112%) as a brown oil.
  • 4
  • [ 66655-67-2 ]
  • [ 1575-61-7 ]
  • 6-(5-chloropentanoyl)-3,4-dihydro-2(1H)-quinazoline [ No CAS ]
YieldReaction ConditionsOperation in experiment
Reference Example 177 6-(5-Chloropentanoyl)-3,4-dihydro-2(1H)-quinazoline Using 3,4-dihydro-2(1H)-quinazoline (4.0 g) and 5-chlorovaleryl chloride (8.37 g) according to the same method as that of Reference Example 1, the title compound was obtained as colorless crystals (3.9 g) 1H NMR (200MHz, DMSO-d6) delta 1.73 (4H, m), 2.96 (2H, t, J = 7.0 Hz), 3.67 (2H, t, J = 6.4 Hz), 4.38 (2H, s), 6.83 (1H, d, J = 8.8 Hz), 7.01 (1H, s), 7.75-7.80 (2H, m), 9.44 (1H, s). MS m/z: 267 [M+H]+
  • 5
  • [ 1575-61-7 ]
  • [ 1267610-26-3 ]
  • 5-chloropentanoic acid [4-(5-morpholin-4-yl-6-oxo-3,6-dihydro-2H-pyridin-1-yl)phenyl]amide [ No CAS ]
YieldReaction ConditionsOperation in experiment
96.08% With tetrabutylammomium bromide; sodium hydroxide; In dichloromethane; water; at 0 - 5℃; for 1h; A solution of 5-chlorovaleroyl chloride (CVC, 82 gm, 0.5273 mol) in MDC (100 ml) was added to the suspension of product of example-IV (125 gm, 0.4573 mol), sodium hydroxide (22 gm, 0.55 mol), TBAB (3.75 gm) in MDC (1150 ml) and Water (49 ml) at 0-5 C. over 1 hrs. The mixture was slowly brought to 25 to 30 C., 300 ml water was added to the reaction mass and stirred for 10 min. Organic layer was separated and washed with water (200 ml), dried over anhydrous sodium sulfate and distilled atmospherically at 50 C. to get a residue. The residue was purified in EtOAc to get pale yellow solid. Yield: 172 gm, 96.08%
89.5% With N-ethyl-N,N-diisopropylamine; In tetrahydrofuran; at 10 - 25℃;Inert atmosphere; The 1e (10.0g, 36.6mmol) was dissolved in tetrahydrofuran (200ml) was added N, N-diisopropylethylamine (7.0g, 54.3mmol), under ice-cooling, a solution of 5-chloro-valeryl chloride (and 7.37 g, 47.6 mmol) to obtain a reaction mixture, said reaction mixture at room temperature overnight. Tracking progress of the reaction by TLC, the reaction was completed, water was added to the reaction solution, separated, washed with water three times, dried over anhydrous magnesium sulfate, filtered, and the solvent was removed by distillation under reduced pressure 1f (12.8g, yellow solid), yield rate: 89.5%
  • 8
  • [ 1575-61-7 ]
  • [ 36725-28-7 ]
  • C16H19N3O2 [ No CAS ]
  • 9
  • [ 1575-61-7 ]
  • [ 36725-28-7 ]
  • C16H20ClN3O2 [ No CAS ]
YieldReaction ConditionsOperation in experiment
With triethylamine; In chloroform; at 0 - 20℃; for 0.5h; To 50 mg of (R)-6-(4-aminophenyl)-5-methyl-4,5-dihydropyridazin-3(2H)- one (0.25 mmol) dissolved in 2.0 mL THF and cooled to 0 C was added 51 of triethylamine (0.37 mmol) and 5-chlorovaleryl chloride (35 mu, 0.27 mmol). The reaction was stirred while slowly warming to room temperature. After 30 min, the reaction mixture was filtered over Celite and concentrated. The crude material was dissolved in 6 mL of DMF, 102 mg of K2C03 (0.74 mmol) was added before heating at 60 C for 3 h. After cooling, water was added and rinsed several times first with EtOAc and then with 1 :9 MeOH:CH2Cl2. The combined organic washes were dried, concentrated, and chromatographed with 0-35% EtOAc in hexane to yield 68 mg of product (97%). XH NMR (300 MHz, CDC13) delta 9.42 (s, 1H), 7.79 (d, J= 8.7, 2H), 7.33 (d, J= 8.7, 2H), 3.66 (d, J = 5.4, 2H), 3.34 (p, J= 7.3, 1H), 2.69 (dd, J= 6.8, 16.9, 1H), 2.59 (t, J= 6.0, 2H), 2.46 (d, J= 16.9, 1H), 2.02 - 1.89 (m, 4H), 1.24 (d, J= 7.4, 3H). 13C NMR (75 MHz, CDC13) delta 169.97, 166.70, 153.08, 144.46, 132.44, 126.50, 125.97, 51.12, 33.70, 32.78, 27.81, 23.32, 21.21, 16.04. MS: 286 (M
  • 10
  • [ 1575-61-7 ]
  • [ 1267610-26-3 ]
  • [ 545445-44-1 ]
YieldReaction ConditionsOperation in experiment
94.27% A solution of 5-chlorovaleroyl chloride (CVC, 82 gm, 0.5273 mol) in MDC (100 ml) was added to the suspension of product of example-IV (125 gm, 0.4573 mol), sodium hydroxide (22 gm, 0.55 mol), TBAB (3.75 gm) in MDC (1150 ml) and Water (49 ml) at 0-5 C. over 1 hr. The mixture was slowly brought to 25 to 30 C., and then the aq. solution of KOH (187 gm, 3.33 mol in 311 ml water) was added slowly in 10-15 min and stirred for 8-10 hrs at room temperature. 300 ml water was added to the reaction mass and stirred for 10 min. Organic layer was separated, washed with water (300 ml) and distilled at 50 C. to get a solid product. Recrystallization of the solid from EtOAc afforded the desired product as a buff colored solid. Yield: 153 gm, 94.27% Purity: 98+%; MP 204-206 C.
89% Compound 3 (27 · 3 g, 0.1 mol), 546 mL of dichloroethane was added to a three-necked flask, cooled to 0 C in an ice bath, tetraethylammonium hydroxide (103 g, 0.7 mol) was added, and stirred for 10 min in an ice bath. Then, 5-chlorovaleryl chloride (18.6 g, 0.12 mol) was added dropwise, and the temperature was controlled at 0 to 5 C. After the completion of the dropwise addition, the ice bath was heated to reflux (80 to 85 C), and the reaction was carried out for 5 hours. The reaction materials and the intermediate state were monitored. The synthesis solution was cooled to room temperature, washed with 500 mL of water, and the organic phase was dried over anhydrous sodium sulfate and concentrated. The residue was recrystallized from acetonitrile to give 31.6 g of Compound 1 as a yellow solid.Its yield: 89%.
87.5% 2 g compound C (compound Ib) and 50 ml acetonitrile were added into a three-necked flask to obtain a turbid solution. The turbid solution was stirred and cooled to 0 C. in an ice bath. 1.75 g (6 eq) sodium hydroxide was added and stirred in the ice bath for 10 min. Then 1.9 ml of 5-chloro-valeryl chloride (2 eq) (diluted with 2 ml acetonitrile) was dropwise added while controlling the temperature to 0-5 C. After completing the addition, the ice bath was removed and the temperature was naturally raised to 30 C. The reaction was performed for 5 hours. After observing the absence of the starting material and the intermediate state of the reaction, the reaction solution was cooled to 0 C. in an ice bath, and adjusted to a neutral pH with 6 N of hydrochloric acid. The reaction solution was concentrated to dryness, pulpifying for 1 hour after adding 8 ml saturated sodium bicarbonate solution, and filtered to obtain 2.29 g yellow solid. Yield: 87.5%. Purity: 95.3% (HPLC). EI-MS (m/z): 355.2. HNMR (400 MHz, DMSO, ppm) delta7.32 (d, J=8.8 Hz, 2H), 7.26 (d, J=8.8 Hz, 2H), 5.71 (t, J=4.8 Hz, 1H), 3.72-3.69 (m, 2H), 3.65-3.63 (m, 4H), 3.60-3.57 (m, 2H), 2.79-2.77 (m, 4H), 2.44-2.41 (m, 2H), 2.40-2.39 (m, 2H), 1.88-1.82 (m, 4H).
86.8% A 4-neck round bottom flask was charged with 80 g of said compound of formula (X) (1.0 eq.) (prepared as said above and containing the impurities of formula (VI) and (VII)), then with 68,3 g of triethylamine (TEA) (2.3 equiv.) and 800 mL of tetrahydrofuran (THF). A solution of 68.3 g of chlorovaleryl chloride (1 ,5 equiv.) in 160 mL of THF was dosed within 1 -2 hours at T=0/5C. The mixture is stirred at T=0/5C for additional 30 minutes, thereafter maintaining the same temperature, a solution of 98,1 g of potassium tert- butoxide (3.0 eq.) in 400mL of THF is dosed over 30-45 minutes. After 30 minutes stirring at T=0/5C, the mixture is warmed to T=20/25C for additional 2 hours. Once checked for reaction completion, the batch is distilled at reduced pressure and Tmax=35C to residual 6 volumes (480 mL) and then stripped with 560 mL of ethanol under the same conditions, again to residual 6 volumes (480 mL). The resulting mixture is diluted with 720 mL of ethanol and 880 mL of water, then the opalescent solution obtained is heated to T=40/45C and filtered on dicalite, washing with 80 mL of pre-heated ethanol (this solid cake is the starting material of the example 3). The filtered solution is distilled under reduced pressure to residual 6 volumes (480 mL). The mixture is cooled down to T=20/25C and stirred at this temperature for at least 1 hour. The slurry is finally filtered washing the wet cake with water (2 x 80 mL). Upon drying at reduced pressure and T=65C for at least 8 hours, 90.3 g of the compound of formula (IX)are obtained, (molar yield 86.8%). This solid contained the following dimer impurities: - 0,04% (HPLC A/A%) dimer impurity of formula (VI), - 0,09% (HPLC A/A%) dimer impurity of formula (VII).
72% Room temperature, Compound 7 (5.8 g, 0.322 mmol), triethylamine 10. 6ml, tetrahydrofuran 176ml added to the reaction flask, stirring, cooling to 0 C, 5-chloropentanoyl chloride (5. 9g) Reaction lh; 0 C conditions, Sodium hydride (2 g, 0.083 mol) was added, Warm to Room temperature reaction 3h, The organic phase was washed with saturated brine once, dried over anhydrous magnesium sulfate, filtered and the solvent was evaporated to give a pale yellow solid. 15.3 g, nil Water ethanol recrystallization was a white solid, after drying 8. 2g, 0.023mol. Yield 72%, m.p. 202-204 C. HPLC: 99. 47% (instrument: Waters high performance liquid chromatography, column: C18, column length: 25 cm, mobile phase: water: Flow rate: l.Oml / min, wavelength: 254nm, column temperature: 30 C, injection volume: 10mu1)
5.2 g Add 150 mL of dichloromethane to a 250 mL four-neck reaction flask.1.6 g of triethylamine and 3.5 g of starting material SM-1.Add 2.4g of SM-2 raw material under ice bath,After the dropwise addition, control the internal temperature to 10-30 C for 1 hour.4.5g of sodium ethoxide was subsequently solid,Add to reaction flask.The temperature was raised to 10-30 C, and the reaction was stirred for 2 hours.After the reaction was completed, 100 mL of drinking water was added.Stir for 30 minutes and pour into the separatory funnel for layering.The upper aqueous solution was extracted once with 100 mL of dichloromethane.The lower organic phases were combined and concentrated to give 5.2 g of APSB-1 solid.

  • 11
  • [ 1575-61-7 ]
  • [ 156150-67-3 ]
  • C11H11Cl2FO [ No CAS ]
YieldReaction ConditionsOperation in experiment
General procedure: Magnesium powder (1.2 eq) was added to a round-bottom flask and flame-dried under vacuum. Once cooled down to room temperature, the vessel was back-filled with nitrogen, a crystal of iodine was added and the flask was flame-dried again under vacuum to sublime the iodine. Once the flask has cooled down to room temperature, THF (1.0 M vs. aryl iodide) was added followed by the aryl iodide (1.0 eq). The resulting suspension was then refluxed for 30 min before being cooled down to room temperature and then 0 C.A separate flask was flame-dried under vacuum and back-filled with nitrogen before being charged with CuI (1.1 eq) and 4-chlorobutyryl chloride (n=1, 1.1 eq) or 5-chlorovaleryl chloride (n=2, 1.1 eq) or 6-chlorocaproyl chloride (n=3, 1.1 eq) in THF (0.5 M vs. aryl iodide) and cooled down to 0 C. To this solution was slowly transferred via cannula under nitrogen the freshly prepared Grignard reagent. The resulting mixture was allowed to warm up to room temperature and stirred until completion (approximately 2 hours) as determined by mass spectral analysis. Upon completion, the reaction mixture was quenched with saturated aqueous NH4Cl and extracted with diethyl ether (3 times). The combined organic layers were washed with saturated aqueous NaCl, dried over Na2SO4, filtered and the volatiles were evaporated under reduced pressure. The crude residue was purified by flash chromatography on silica.
  • 12
  • [ 1575-61-7 ]
  • [ 120068-37-3 ]
  • C17H10Cl2F6N4O2S [ No CAS ]
YieldReaction ConditionsOperation in experiment
(1) 10 mmol of <strong>[120068-37-3]fipronil</strong> was added to a 100 mL flask, and 30 mL of tetrahydrofuran was added as a solvent to add a magnetic stirrer.mix. Slowly add 20 mmol of NaH to the batch under stirring, continue stirring for 20 min after the addition, and then add to it.10mmol 5-chlorovaleryl chloride, then heated at 80 C for 12h under reflux, after the reaction is completed, the excess solvent is removed by rotary evaporation, using 50mL BExtraction with ethyl acetate and 120 mL of saturated Na2CO3 solution, collecting the organic phase, adding 5 g of silica gel powder to it, and spinning it to dryness.The sample was applied and purified by silica gel column chromatography using petroleum ether and ethyl acetate in a volume ratio of 4:1.1-(2,6-Dichloro-4-trifluoromethyl-phenyl)-5-(hexacyclic imide-1-yl)-4-trifluoromethyl-1H-pyrazole-3-carbonitrile.
 

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