Acetic Anhydride → HCID 18355274, compound

HRID 1533813Notes

Reaction equation

HRID 1533813 reaction equation
[NH2:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][CH:5]=[CH:4][C:3]=1[C:11]([NH:13][C:14]1[CH:31]=[CH:30][C:17]([C:18]([N:20]([C:22]2[CH:27]=[CH:26][C:25]([CH3:28])=[CH:24][C:23]=2[OH:29])[CH3:21])=[O:19])=[CH:16][C:15]=1[O:32][CH3:33])=[O:12].[C:34](OC(=O)C)(=[O:36])[CH3:35].C(N(CC)CC)C>ClCCl.C(Cl)(Cl)Cl>[C:34]([O:29][C:23]1[CH:24]=[C:25]([CH3:28])[CH:26]=[CH:27][C:22]=1[N:20]([CH3:21])[C:18](=[O:19])[C:17]1[CH:30]=[CH:31][C:14]([NH:13][C:11]([C:3]2[CH:4]=[CH:5][CH:6]=[C:7]([N+:8]([O-:10])=[O:9])[C:2]=2[NH2:1])=[O:12])=[C:15]([O:32][CH3:33])[CH:16]=1)(=[O:36])[CH3:35]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 18354972HCID 18354972, compound

Product 1

HCID 18355274HCID 18355274, compoundYield 97.2%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 4-(2-amino-3-nitrophenyl)carbonylamino-N-(2-hydroxy-4-methylphenyl)-3-methoxy-N-methylbenzamide (400 mg), acetic anhydride (90.7 mg) and triethylamine (89.9 mg) in dichloromethane (20 ml) was stirred in an ice bath for 4 hours. The mixture was diluted with chloroform and the solution was washed with water and brine. The organic phase was dried over magnesium sulfate and the solvent was evaporated in vacuo to give N-(2-acetoxy-4-methylphenyl)-4-(2-amino-3-nitrophenyl)carbonylamino-3-methoxy-N-methylbenzamide (425 mg).

Workup

  1. washthe solution was washed with water and brine
  2. dry with materialThe organic phase was dried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-c194d9e18b2642eba3b041135ef37d5b
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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