Ammonia → Nordiazepam

HRID 1973064

반응식

HRID 1973064 반응식
C1N2CN3CN(C2)C[N:2]1C3.[OH-].[NH4+].Cl[CH2:14][C:15]([NH:17][C:18]1[CH:31]=[CH:30][C:29]([Cl:32])=[CH:28][C:19]=1[C:20]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=O)=[O:16].N>C(O)C>[Cl:32][C:29]1[CH:30]=[CH:31][C:18]2[NH:17][C:15](=[O:16])[CH2:14][N:2]=[C:20]([C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)[C:19]=2[CH:28]=1

참가 물질

6

반응물 4

HCID 222Ammonia2회HCID 4101HexamethylenetetramineHCID 14923Ammonium HydroxideHCID 776355-Chloro-2-(chloroacetamido)benzophenone

생성물 1

HCID 2997Nordiazepam수율 167%

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

A mixture of ethanol (1100 ml), hexamethylenetetramine (70.0 g., 0.5 mol), 26% ammonium hydroxide (58 ml) and 2-chloroacetamido-5-chlorobenzophenone (308.2 g., 1.0 mol) was stirred and slowly heated to reflux with ammonia bubbling into the mixture. Reflux was continued for 5 hours, the flow of ammonia was interrupted, and the reaction mixture distilled to dryness in vacuo. The residue was heated to reflux for 30 minutes in a mixture of toluene (500 mls) and water (500 mls) and then allowed to cool slowly to room temperature. The crystalline material was filtered, washed with toluene (100 mls) and hot water (2 × 250 mls) and dried to constant weight. The product, 7-chloro-1,3-dihydro-5-phenyl-2H-1,4-benzodiazepin-2-one (226 g) obtained corresponded to a yield of 83.5%, melting point 210° C.

후처리

  1. temperatureslowly heated
  2. temperatureReflux
  3. distillationthe reaction mixture distilled to dryness in vacuo
  4. temperatureThe residue was heated
  5. temperatureto reflux for 30 minutes in a mixture of toluene (500 mls) and water (500 mls)
  6. filtrationThe crystalline material was filtered
  7. washwashed with toluene (100 mls) and hot water (2 × 250 mls)
  8. customdried to constant weight

출처 및 근거

ORD 기록
ord-2518b212b6f642098e18a46d46582765
출처 데이터셋
uspto-grants-1976_12
특허 번호
US03996209

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