4-Aminophenol → HCID 15629745, compound

HRID 2259981Notes

Reaction equation

HRID 2259981 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5](O)=[CH:4][CH:3]=1.[H-].[Na+].[C:11]1([CH3:17])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1.C1(N[C:25](=[O:28])[CH2:26]Cl)C=CC=CC=1.CN(C)C=[O:32]>>[C:2]1([NH:1][C:14]2[CH:15]=[CH:16][C:11]([C:17]([O:28][CH2:25][CH3:26])=[O:32])=[CH:12][CH:13]=2)[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

6

Reactant 5

HCID 4034-AminophenolHCID 1140TolueneHCID 6228Dimethylformamide3×HCID 11485ChloroacetanilideHCID 24758Sodium hydride2×

Product 1

HCID 15629745HCID 15629745, compound

Procedure

30.2 g of 4-aminophenol was dissolved in 130 ml of N,N-dimethylformamide, followed by the addition of 11.64 g of 57% NaH and agitated at room temperature for 30 rain to obtain a N,N-dimethylformamide solution. 130 ml of toluene and 10.5 g of 57% NaH were added to 41 g of 4-hydroxy ethylbenzoate. After agitation, 45 g of N-phenyl chloroacetamide and 8.7 ml of N,N-dimethylformamide were also added. The toluene recovered from the reflux was reacted with the above N,N-dimethylformamide solution. After that, the N,N-dimethylformamide was recovered and extracted with toluene. 47 g of ethyl 4-phenylaminobenzoate was obtained when the toluene layer of the extraction process was dehydrated with magnesium sulfate. The product yield was 79%.

Workup

  1. customThe toluene recovered from the reflux
  2. customwas reacted with the above N,N-dimethylformamide solution
  3. customAfter that, the N,N-dimethylformamide was recovered
  4. extractionextracted with toluene

Sources & evidence

ORD record
ord-75b8fcde260c4f269428966e00a6bae7
Source dataset
uspto-grants-1995_12
Patent number
US05475139

Reaction notes

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