Acetic Acid → 9-Chloro-7-[2-(2,4-di-t-amylphenoxy)butanoylamino]-6-hydroxy-1,5-benzodiazepin-2,4-dione

HRID 1253013Notes

Reaction equation

HRID 1253013 reaction equation
[C:1]([NH:4][C:5]1[C:6]([N+:36]([O-])=O)=[C:7]([OH:35])[C:8]([NH:12][C:13](=[O:34])[CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:27][CH3:28])([CH3:26])[CH3:25])=[CH:20][C:19]=2[C:29]([CH2:32][CH3:33])([CH3:31])[CH3:30])[CH2:15][CH3:16])=[CH:9][C:10]=1[Cl:11])(=[O:3])[CH3:2].[OH-].[Na+].O.[C:42](O)(=[O:44])C>CO>[Cl:11][C:10]1[C:5]2=[N:4][C:1](=[O:3])[CH2:2][C:42](=[O:44])[N:36]=[C:6]2[C:7]([OH:35])=[C:8]([NH:12][C:13](=[O:34])[CH:14]([O:17][C:18]2[CH:23]=[CH:22][C:21]([C:24]([CH2:27][CH3:28])([CH3:25])[CH3:26])=[CH:20][C:19]=2[C:29]([CH2:32][CH3:33])([CH3:30])[CH3:31])[CH2:15][CH3:16])[CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962Water2×HCID 14798Sodium HydroxideHCID 201378243-Acetylamino-4-chloro-2-nitro-6-[2-(2,4-di-t-amylphenoxy)butanoylamino]phenol

Product 1

HCID 1355831249-Chloro-7-[2-(2,4-di-t-amylphenoxy)butanoylamino]-6-hydroxy-1,5-benzodiazepin-2,4-dione

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

In 200 ml of methanol was dispersed 40 g of the 3-acetylamino-4-chloro-2-nitro-6-[2-(2,4-di-t-amylphenoxy)butanoylamino]phenol, and the dispersion was stirred while refluxing for 5 hours together with 9 g of sodium hydroxide and 40 ml of water. The reaction mixture was cooled to room temperature and then poured into 300 ml of water. Upon dropwise addition of 15 ml of acetic acid, red crystals were precipitated. The crystals were collected by filtration, recrystallized from acetonitrile, and dried to provide 21 g of the desired compound.

Workup

  1. customwere precipitated
  2. filtrationThe crystals were collected by filtration
  3. customrecrystallized from acetonitrile
  4. customdried

Sources & evidence

ORD record
ord-878e9f1b10144bd7971158454fcf9b16
Source dataset
uspto-grants-1988_05
Patent number
US04746602

Reaction notes

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