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

HRID 1253014Notes

Reaction equation

HRID 1253014 reaction equation
[NH2:1][C:2]1[C:3]([N+:33]([O-])=O)=[C:4]([OH:32])[C:5]([NH:9][C:10](=[O:31])[CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:24][CH3:25])([CH3:23])[CH3:22])=[CH:17][C:16]=2[C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])[CH2:12][CH3:13])=[CH:6][C:7]=1[Cl:8].S(S([O-])=O)([O-])=O.[Na+].[Na+].[OH2:44]>C(O)(C)C>[Cl:8][C:7]1[C:2]2=[N:1][C:11](=[O:14])[CH2:12][C:13](=[O:44])[N:33]=[C:3]2[C:4]([OH:32])=[C:5]([NH:9][C:10](=[O:31])[CH:11]([O:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH2:24][CH3:25])([CH3:22])[CH3:23])=[CH:17][C:16]=2[C:26]([CH2:29][CH3:30])([CH3:28])[CH3:27])[CH2:12][CH3:13])[CH:6]=1

Participants

5

Reactant 3

HCID 962WaterHCID 24489Sodium DithioniteHCID 201378153-Amino-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 3776IsopropanolSolvent

Procedure

In a mixture of 200 ml of water and 40 ml of isopropanol was dispersed 20 g of the 3-amino-4-chloro-2-nitro-6-[2-(2,4-di-t-amylphenoxy)butanoylamino]phenol prepared in (4) above, and 100 g of sodium hydrosulfite was slowly added to the dispersion while stirring and heating on a steam bath. After refluxing, the reaction mixture was concentrated, and the precipitated solid was collected by filtration, washed with water, and dried to provide 17 g of the desired compound.

Workup

  1. temperatureheating on a steam bath
  2. temperatureAfter refluxing
  3. concentrationthe reaction mixture was concentrated
  4. filtrationthe precipitated solid was collected by filtration
  5. washwashed with water
  6. customdried

Sources & evidence

ORD record
ord-21513b6796d64d7cb4df54d5c9578c45
Source dataset
uspto-grants-1988_05
Patent number
US04746602

Reaction notes

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