[ CAS No. 16947-63-0 ]

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2D
Chemical Structure| 16947-63-0
Chemical Structure| 16947-63-0
Structure of 16947-63-0

Quality Control of [ 16947-63-0 ]

Purity: {[proInfo.showProBatch.pb_purity]}

Related Doc. of [ 16947-63-0 ]

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Product Details of [ 16947-63-0 ]

CAS No. :16947-63-0MDL No. :MFCD02093072
Formula :C8H10N2O2Boiling Point :352.6°C at 760 mmHg
Linear Structure Formula :-InChI Key :-
M.W :166.18Pubchem ID :28159
Synonyms :

Computed Properties of [ 16947-63-0 ]

TPSA : 71.8 H-Bond Acceptor Count : 3
XLogP3 : 1.8 H-Bond Donor Count : 1
SP3 : 0.25 Rotatable Bond Count : 0

Safety of [ 16947-63-0 ]

Signal Word:WarningClassN/A
Precautionary Statements:P261-P305+P351+P338UN#:N/A
Hazard Statements:H302-H315-H319-H335Packing Group:N/A
GHS Pictogram:

Application In Synthesis of [ 16947-63-0 ]

  • Upstream synthesis route of [ 16947-63-0 ]

[ 16947-63-0 ] Synthesis Path-Upstream   1~11

  • 1
  • [ 67083-22-1 ]
  • [ 16947-63-0 ]
YieldReaction ConditionsOperation in experiment
100% With sulfuric acid In water at 40℃; K43-c(1.9g, 5.9mmol) and water(0.75mL) were added into a round- bottomed flask, concentrated sulfuric acid(10mL) was added thereto, and the mixture was kept under 40 °C overnight. The mixture was cooled to room temperature,and crushed ice and 2M aqeous sodium hydroxide solution (15mL) were poured thereto. The mixture was extractedwith ethyl acetate(50mL), and the organic phase obtained was washed with water(20mL) twice, and then with saturatedsaline(20mL) once, dried with anhydrous sodium sulfate and concentrated to to give K43-d as a yellow sold(980mg,yield: 100percent), which was directly used in the next step
66% at 60℃; for 1.00 h; A solution of 3 (23 g, 72 mmol, 1.0 eq) in concentrated H2SO4 (232 mL, c = 0.3) was heated to 60 C with stirring for 1 hour. The reaction was then poured into ice (1000 mL), adjusted to pH 8 with 20percent NaOH and extracted with EA (200 mL). The organic phase was washed with brine (15 mL), dried over anhydrous Na2SO4 and filtered to give a residue. The residue after rotary evaporation was purified by column chromatography to give the desired product 4 (8 g, 66percent yield).
53% at 50℃; for 1.00 h; N-Tosyl-2,6-dimethyl-4-nitroaniline (20) (3.2 g, 10.0 mmol) wasdissolved in H2SO4 (32 mL) and warmed at 50 C for 1 h. The reactionmixture was poured slowly into an ice/water mixture. Theprecipitate was filtered and washed with water. The crude productwas purified by recrystallization (ethyl acetate) to give 21 as yellowcrystals (1.0 g, 53percent). Rf: 0.34 (n-hexane/ethyl acetate, 5/1, v/v). Mp:164e165 C. 1H NMR (DMSO-d6, 400 MHz) d 7.79 (s, 2H), 6.16 (s,2H), 2.16 (s, 6H). MS (ESI) m/z: 166.8 [MH], 188.8 [MNa].
Reference: [1] Patent: EP3138833, 2017, A1. Location in patent: Paragraph 0040; 0043
[2] European Journal of Organic Chemistry, 2009, # 5, p. 739 - 748
[3] Journal of Medicinal Chemistry, 1983, vol. 26, # 11, p. 1625 - 1630
[4] Heterocycles, 2008, vol. 76, # 2, p. 1313 - 1328
[5] Patent: KR2018/69782, 2018, A. Location in patent: Paragraph 0422; 0424; 0431-0433
[6] Organic and Biomolecular Chemistry, 2007, vol. 5, # 7, p. 1062 - 1080
[7] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
[8] Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 809,815
  • 2
  • [ 116296-36-7 ]
  • [ 16947-63-0 ]
YieldReaction ConditionsOperation in experiment
97%
Stage #1: at 140℃; for 0.50 h; Microwave irradiation
Stage #2: With sodium carbonate In water
2,6-Dimethyl-4-nitro-phenylamine.; Concentrated hydrochloric acid (17.5 rnL) was added to iV-(2,6-dimethyl-4-nitro-phenyl)- acetamide (5.05 g) and heated to 140 0C for 30 minutes in a sealed microwave process vial. The reaction mixture was neutralized with solid sodium carbonate in water and the precipitated product was collected by filtration and washed with water (100 mL) to furnish 3.93 g (97percent yield) of the title compound as a yellow solid. 1H NMR (500 MHz, DMSOd6): 2.15 (s, 6H), 6.15 (b, 2H), 7.79 (s, 2H).
Reference: [1] Patent: WO2006/29623, 2006, A1. Location in patent: Page/Page column 55
  • 3
  • [ 14150-94-8 ]
  • [ 96-22-0 ]
  • [ 16947-63-0 ]
  • [ 68541-85-5 ]
Reference: [1] European Journal of Organic Chemistry, 2015, vol. 2015, # 6, p. 1203 - 1206
[2] Bulletin of the Chemical Society of Japan, 1990, vol. 63, # 10, p. 2820 - 2827
  • 4
  • [ 4703-15-5 ]
  • [ 16947-63-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 7, p. 1062 - 1080
[2] Canadian Journal of Chemistry, 1988, vol. 66, p. 1454 - 1458
[3] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
[4] Patent: EP3138833, 2017, A1
[5] Patent: KR2018/69782, 2018, A
  • 5
  • [ 87-62-7 ]
  • [ 16947-63-0 ]
Reference: [1] Organic and Biomolecular Chemistry, 2007, vol. 5, # 7, p. 1062 - 1080
[2] Journal of Chemical Research, Miniprint, 2003, # 7, p. 701 - 714
[3] Canadian Journal of Chemistry, 1988, vol. 66, p. 1454 - 1458
[4] European Journal of Medicinal Chemistry, 2017, vol. 131, p. 1 - 13
[5] Patent: EP3138833, 2017, A1
[6] Patent: KR2018/69782, 2018, A
  • 6
  • [ 2423-71-4 ]
  • [ 16947-63-0 ]
Reference: [1] Journal of the American Chemical Society, 1940, vol. 62, p. 2995,3001
  • 7
  • [ 294853-97-7 ]
  • [ 16947-63-0 ]
Reference: [1] Canadian Journal of Chemistry, 1988, vol. 66, p. 1454 - 1458
  • 8
  • [ 99841-87-9 ]
  • [ 16947-63-0 ]
Reference: [1] Acta Chemica Scandinavica (1947-1973), 1957, vol. 11, p. 1350,1354
  • 9
  • [ 855227-21-3 ]
  • [ 16947-63-0 ]
Reference: [1] Recueil des Travaux Chimiques des Pays-Bas, 1954, vol. 73, p. 809,815
  • 10
  • [ 632300-21-1 ]
  • [ 16947-63-0 ]
Reference: [1] Journal of Chemical Research, Miniprint, 2003, # 7, p. 701 - 714
  • 11
  • [ 66236-09-7 ]
  • [ 16947-63-0 ]
Reference: [1] Journal of Chemical Research, Miniprint, 2003, # 7, p. 701 - 714
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