Water → 7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

HRID 651572노트

반응식

HRID 651572 반응식
[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16]#[N:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1.Cl.[NH2:21][OH:22].C[O-].[Na+].O>CN(C)C=O>[Cl:1][C:2]1[C:7]2[C:8](=[O:19])[N:9]([CH3:18])[CH2:10][C:11]3[N:12]([CH:13]=[N:14][C:15]=3[C:16](=[N:21][OH:22])[NH2:17])[C:6]=2[CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 443297Hydroxyamine hydrochlorideHCID 10942334Sodium MethoxideHCID 145904237-chloro-5-methyl-6-oxo-5,6-dihydro-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile

생성물 1

HCID 541588047-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
1 °C

실험 절차

16.8 g 7-Chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carbonitrile were suspended under stirring and argon atmosphere in 101 ml N,N-dimethylformamide and 13.48 g hydroxylamine hydrochloride were added in one portion. 34.2 ml Sodium methanolate were then added over 60 minutes to the yellow suspension, which turned to a colorless suspension. It was stirred one more hour at r.t., then cooled to 0-2° C. and 202 ml deionized water were added over 30 minutes. After stirring one more hour at 0° C., the precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime (VIII)) was filtered off, washed twice with 40 ml deionized water and dried under vacuum at 70° C. for 18 hours. Crude product: 17.84 g as a white powder. m.p. >250° C.

후처리

  1. stirringIt was stirred one more hour at r.t.
  2. additionwere added over 30 minutes
  3. stirringAfter stirring one more hour at 0° C.
  4. filtrationthe precipitate (7-chloro-5,6-dihydro-5-methyl-6-oxo-4H-imidazo[1,5-a][1,4]benzodiazepine-3-carboxamidoxime (VIII)) was filtered off
  5. washwashed twice with 40 ml
  6. customdried under vacuum at 70° C. for 18 hours

출처 및 근거

ORD 기록
ord-3fc77cdd5e9347d4bb8dedd6c5300552
출처 데이터셋
uspto-grants-2001_08
특허 번호
US06281353B1

반응 노트

불러오는 중…