Phenyl acetate → 4-[5-[4-(acetyliminoaminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

HRID 2399955Notes

Reaction equation

HRID 2399955 reaction equation
[NH2:1][N:2]=[CH:3][C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:29]=[CH:28][C:18]([C:19]([N:21]([CH:25]([CH3:27])[CH3:26])[CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:17][C:16]=2[O:30][CH3:31])=[CH:6][CH:5]=1.[C:34](OC1C=CC=CC=1)(=[O:36])[CH3:35]>C(Cl)Cl>[C:34]([N:1]=[N:2][CH2:3][C:4]1[CH:33]=[CH:32][C:7]([O:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][O:14][C:15]2[CH:29]=[CH:28][C:18]([C:19]([N:21]([CH:25]([CH3:26])[CH3:27])[CH:22]([CH3:24])[CH3:23])=[O:20])=[CH:17][C:16]=2[O:30][CH3:31])=[CH:6][CH:5]=1)(=[O:36])[CH3:35]

Participants

4

Reactant 2

HCID 31229Phenyl acetateHCID 1838004-[5-[4-(aminoiminomethyl)phenoxy]pentoxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

Product 1

HCID 189917174-[5-[4-(acetyliminoaminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A stirred solution of 4-[5-[4-(aminoiminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide (40.0 g, 87.7 mmol) in 500 mL anhydrous methylene chloride is treated with phenyl acetate (11.1 mL, 87.7 mmol). The solution is stirred 3 hours, concentrated in vacuo and the resulting liquid is purified by chromatography on silica gel (850 g) with 30% ethyl acetate/hexane as the eluent to afford 4-[5-[4-(acetyliminoaminomethyl)phenoxy]pentyloxy]-3-methoxy-N,N-bis(1-methylethyl)benzamide as a colorless foam; CHN calculated for C28H39N3O5 :

Workup

  1. concentrationconcentrated in vacuo
  2. customthe resulting liquid is purified by chromatography on silica gel (850 g) with 30% ethyl acetate/hexane as the eluent

Sources & evidence

ORD record
ord-dbf332556de64a12a8f6fef2b8f1f906
Source dataset
uspto-grants-1995_09
Patent number
US05451700

Reaction notes

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