Potassium Carbonate → HCID 18522031, compound

HRID 413746Notes

Reaction equation

HRID 413746 reaction equation
[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[NH:6][C:7]1[CH:12]=[CH:11][C:10]([NH2:13])=[CH:9][CH:8]=1)([O-:3])=[O:2].Br[C:19]1[S:20][CH:21]=[CH:22][N:23]=1.C(=O)([O-])[O-].[K+].[K+]>O>[N+:1]([C:4]1[CH:17]=[CH:16][CH:15]=[CH:14][C:5]=1[NH:6][C:7]1[CH:8]=[CH:9][C:10]([NH:13][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[CH:11][CH:12]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 764302-BromothiazoleHCID 18522089N~1~-(2-Nitrophenyl)benzene-1,4-diamine

Product 1

HCID 18522031HCID 18522031, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

2-Nitro-N-(4-aminophenyl)aniline (5.0 g, 21.8 mmol), 2-bromothiazole (3.58 g, 21.8 mmol) and potassium carbonate (3.01 g, 21.8 mmol) was stirred at 150° C. for 24 h. Water (250 ml) was added and the mixture was extracted with ethyl acetate (250 ml). The crude extract was purified by chromatography using silica gel and a mixture of ethanol (4%) and dichloromethane as eluent. The product was isolated as the free base. Yield 1.47 g, 22%. M.p. 195-197° C.

Workup

  1. extractionthe mixture was extracted with ethyl acetate (250 ml)
  2. extractionThe crude extract
  3. customwas purified by chromatography
  4. additiona mixture of ethanol (4%) and dichloromethane as eluent
  5. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-b943d2f692d7496bb5c34628cc134880
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Reaction notes

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