Acetic Anhydride → HCID 18355307, compound

HRID 1533815Notes

Reaction equation

HRID 1533815 reaction equation
[NH2:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]([CH3:38])[C:15](=[O:37])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH3:34])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])=[C:18]([O:35][CH3:36])[CH:17]=1.[C:39](OC(=O)C)(=[O:41])[CH3:40]>ClCCl>[C:39]([NH:1][CH2:2][CH2:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[C:11]([CH3:13])[CH:10]=[CH:9][C:8]=1[N:14]([CH3:38])[C:15](=[O:37])[C:16]1[CH:21]=[CH:20][C:19]([NH:22][C:23]([C:25]2[C:33]3[N:32]=[C:31]([CH3:34])[NH:30][C:29]=3[CH:28]=[CH:27][CH:26]=2)=[O:24])=[C:18]([O:35][CH3:36])[CH:17]=1)(=[O:41])[CH3:40]

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 18354848HCID 18354848, compound

Product 1

HCID 18355307HCID 18355307, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of N-[2-(4-aminobut-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)carbonylaminobenzamide (120 mg) in dichloromethane (10 ml) was added acetic anhydride (23.8 mg) and the mixture was stirred at ambient temperature for 1 hour. The solution was washed with water and brine and dried over magnesium sulfate and the solvent was evaporated in vacuo. The residue was purified by silica gel column (2% methanol in chloroform) and the product was solidified with diethyl ether to give N-[2-(4-acetylaminobut-1-yloxy)-4-methylphenyl]-3-methoxy-N-methyl-4-(2-methyl-1H-benzimidazol-4-yl)carbonylaminobenzamide (87 mg).

Workup

  1. washThe solution was washed with water and brine
  2. dry with materialdried over magnesium sulfate
  3. customthe solvent was evaporated in vacuo
  4. customThe residue was purified by silica gel column (2% methanol in chloroform)

Sources & evidence

ORD record
ord-9d10a0e4326245779d8f1d5dc2e24120
Source dataset
uspto-grants-2001_03
Patent number
US06207693B1

Reaction notes

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