Sodium Hydroxide → HCID 13175739, compound

HRID 1981970Notes

Reaction equation

HRID 1981970 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 upon 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-194cb20eb8494a1b8e5d32d2a9fddbe5
Source dataset
uspto-grants-1986_06
Patent number
US04594436

Reaction notes

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