Ethylene Oxide → 10-chloro-11b-phenyl-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7H)-one-5-carboxylic acid ethyl ester

HRID 597630Notes

Reaction equation

HRID 597630 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:9]=2[NH:8][C:7]1=[O:24])=[O:5])[CH3:2].[CH2:25]1[O:27][CH2:26]1.[OH-].[NH4+]>C(Cl)CCl>[CH2:1]([O:3][C:4]([CH:6]1[N:12]2[CH2:25][CH2:26][O:27][C:11]2([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10]2[CH:19]=[C:20]([Cl:23])[CH:21]=[CH:22][C:9]=2[NH:8][C:7]1=[O:24])=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 6354Ethylene OxideHCID 14923Ammonium HydroxideHCID 110682Ethyl 7-chloro-2,3-dihydro-2-oxo-5-phenyl-1H-1,4-benzodiazepine-3-carboxylate

Product 1

HCID 5391709210-chloro-11b-phenyl-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7H)-one-5-carboxylic acid ethyl ester

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent2×

Procedure

To a solution of 3.1 g. (0.0118 M) of stannic chloride in 35 ml. of dry ethylene dichloride under nitrogen was added 1.5 g. (0.00438 M) of 7-chloro-1,3-dihydro-2-oxo-5-phenyl-2H-1,4-benzodiazepine-3-carboxylic acid ethyl ester. The reaction was stirred in an ice bath, when a solution of 1.0 g. (0.0233 M) of ethylene oxide in 5 ml. of ethylene dichloride was added. The mixture was stirred at room temperature for 3 hr. and then made basic with mixture of ammonium hydroxide and ice. The mixture was filtered, and the filtrate was dried with anhydrous sodium sulfate and evaporated to dryness. The residue was crystallized from ether. Recrystallization from a mixture of dichloromethane and petroleum ether gave 10-chloro-11b-phenyl-2,3,5,11b-tetrahydrooxazolo[3,2-d] [1,4]benzodiazepin-6(7H)-one-5-carboxylic acid ethyl ester as white rods, m.p. 205°-207°.

Workup

  1. stirringThe mixture was stirred at room temperature for 3 hr
  2. filtrationThe mixture was filtered
  3. dry with materialthe filtrate was dried with anhydrous sodium sulfate
  4. customevaporated to dryness
  5. customThe residue was crystallized from ether
  6. customRecrystallization
  7. additionfrom a mixture of dichloromethane and petroleum ether

Sources & evidence

ORD record
ord-925c261a474644afbb38283e50d7c647
Source dataset
uspto-grants-1977_03
Patent number
US04014916

Reaction notes

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