Diazepam → 10-chloro-2-chloromethyl-2,3,5,11b-tetrahydro-7-methyl-11b-phenyloxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one

HRID 1973522

Reaction equation

HRID 1973522 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]=[C:7]([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1.[Cl-].[Al+3].[Cl-].[Cl-].[Cl:25][CH2:26][CH:27]1[O:29][CH2:28]1>C1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[CH2:9][N:8]3[CH2:28][CH:27]([CH2:26][Cl:25])[O:29][C:7]3([C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 3016DiazepamHCID 7835EpichlorohydrinHCID 6451240Aluminum(III) Chloride

Product 1

HCID 2140997110-chloro-2-chloromethyl-2,3,5,11b-tetrahydro-7-methyl-11b-phenyloxazolo[3,2-d][1,4]benzodiazepin-6(7H)-one

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent3×

Procedure

A mixture of 10g. (35 mmole) of 7-chloro-1,3-dihydro-1-methyl-5-phenyl-2H-1,4-benzodiazepin-2-one, 10 g. of aluminum chloride, and 200 ml. of dried benzene was treated with 30 ml. of 1-chloro-2,3-epoxypropane in 100 ml. of benzene. The reaction mixture was stirred overnight. Work-up as in Method A, Example 5, above gave 32 g. of a crude oil. The oil was dissolved in benzene, filtered over Florisil, evaporated to dryness and crystallized from ether-petroleum ether to give the above-titled product as colorless needles, m.p. 140°-142°.

Workup

  1. filtrationfiltered over Florisil
  2. customevaporated to dryness
  3. customcrystallized from ether-petroleum ether

Sources & evidence

ORD record
ord-48d65ea8b3314be491d6c9e20163f5e3
Source dataset
uspto-grants-1976_12
Patent number
US03997591

Linked notes

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