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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 1658607
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HRID 1658607 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

5

반응물 3

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

생성물 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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매2회

실험 절차

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°.

후처리

  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

출처 및 근거

ORD 기록
ord-dc58b00827e843ad98bc56d92a867745
출처 데이터셋
uspto-grants-1976_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US03965151

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