Sodium Hydroxide → HCID 13175723, compound

HRID 1981969Notes

Reaction equation

HRID 1981969 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[C:7]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[N:8][CH2:9][CH:10]3[CH2:15][O:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1.ClC1C=CC=C(C(OO)=[O:31])C=1.[OH-].[Na+]>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[C:7]([C:16]3[O:17][CH:18]=[CH:19][CH:20]=3)=[N+:8]([O-:31])[CH2:9][CH:10]3[CH2:15][O:14][CH2:13][CH2:12][N:11]3[C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 70297m-Chloroperbenzoic acidHCID 13175691HCID 13175691, compound

Product 1

HCID 13175723HCID 13175723, compoundYield 36.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 6 g of 1,2,4,4a-tetrahydro-10-methoxy-7-(2-furyl)-5H-[1,4]oxazino[4,3-a][1,4]benzodiazepine (for the preparation, see Example 2) in 100 ml of methylene chloride is heated under reflux with 4.2 g of 3-chloroperbenzoic acid for 3 hours. The reaction solution is then rendered alkaline with aqueous dilute sodium hydroxide solution and is worked up in the customary manner. The crude product isolated is purified by chromatography on aluminum oxide of activity level II, using methylene chloride, and is crystallised from isopropanol. 2.3 g of 1,2,4,4a-tetrahydro-10-methoxy-7-(2-furyl)-5H-[1,4]oxazino[4,3-a][1,4]benzodiazepine 6-oxide are obtained. Melting point: 183° to 186° C.

Workup

  1. temperatureis heated
  2. customThe crude product isolated
  3. customis purified by chromatography on aluminum oxide of activity level II
  4. customis crystallised from isopropanol

Sources & evidence

ORD record
ord-aa7ef7315139402eb377150dce106858
Source dataset
uspto-grants-1986_06
Patent number
US04594436

Reaction notes

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