Sodium Hydroxide → HCID 13175739, compound

HRID 1980241Notes

Reaction equation

HRID 1980241 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][Cl:14])[CH:10]([CH2:15][Cl:16])[CH2:9][N:8]=[C:7]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:6]=2[CH:22]=1.ClC1C=CC=C(C(OO)=[O:31])C=1.[OH-].[Na+]>C(Cl)Cl>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13][Cl:14])[CH:10]([CH2:15][Cl:16])[CH2:9][N+:8]([O-:31])=[C:7]([C:17]3[O:18][CH:19]=[CH:20][CH:21]=3)[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 13175737HCID 13175737, compound

Product 1

HCID 13175739HCID 13175739, compoundYield 69.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 17.8 g of 7-chloro-1-(β-chloroethyl)-2-chloromethyl-5-(2-furyl)-2,3-dihydro-1H-1,4-benzodiazepine in 250 ml of methylene chloride is heated under reflux with 10.4 g of 3-chloroperbenzoic acid for 2 hours. The reaction solution is then rendered alkaline with aqueous dilute sodium hydroxide solution and is worked up in the customary manner, and the reaction product is isolated and then purified by chromatography on aluminium oxide of activity level II, using methylene chloride, and crystallised from methanol. 13 g of 7-chloro-1-(β-chloroethyl)-2-chloromethyl-5-(2-furyl)-2,3-dihydro-1H-1,4-benzodiazepine-4-oxide are obtained. Melting point: 158° to 159° C.

Workup

  1. customthe reaction product is isolated
  2. custompurified by chromatography on aluminium oxide of activity level II
  3. customcrystallised from methanol

Sources & evidence

ORD record
ord-7f74056f386d432496910243139274e1
Source dataset
uspto-grants-1985_04
Patent number
US04508716

Reaction notes

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