Chloroform → HCID 13175690, compound

HRID 1981968Notes

Reaction equation

HRID 1981968 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH2:12][CH2:13]Cl)[CH:10]([CH2:15]Cl)[CH2:9][N:8]=[C:7]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[C:6]=2[CH:22]=1.[OH-:23].[Na+].C(Cl)(Cl)Cl>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[CH2:12][CH2:13][O:23][CH2:15][CH:10]3[CH2:9][N:8]=[C:7]([C:17]3[CH:21]=[CH:20][S:19][CH:18]=3)[C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 6212ChloroformHCID 14798Sodium HydroxideHCID 13175689HCID 13175689, compound

Product 1

HCID 13175690HCID 13175690, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 11 g of 7-chloro-1-(β-chloroethyl)-2-chloromethyl-5-(3-thienyl)-2,3-dihydro-1H-1,4-benzodiazepine in 60 ml of dioxane and 160 ml of 4.5% strength sodium hydroxide solution is heated under reflux for 5 hours. After the solvent has been stripped off in vacuo, the reaction product is isolated from chloroform and is then chromatographed on aluminum oxide of activity level II, using methylene chloride. After the methylene chloride has been stripped off, 6.5 g of 1,2,4,4a-tetrahydro-9-chloro-7-(3-thienyl)-5H-[1,4]oxazino[4,3-a][1,4]benzodiazepine are obtained as an oil. This product is converted into its hydrochloride by reaction with alcoholic hydrogen chloride solution, and the product is crystallised as the hydrochloride.0.3H2O from isopropanol. Melting point: 207° to 212° C.

Workup

  1. temperatureunder reflux for 5 hours
  2. customis then chromatographed on aluminum oxide of activity level II

Sources & evidence

ORD record
ord-0c3cc1e3a1934b41ad6f2eacfaa0d817
Source dataset
uspto-grants-1986_06
Patent number
US04594436

Reaction notes

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