Bromine → 7-amino-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

HRID 354748

반응식

HRID 354748 반응식
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[CH:23]=1.[Br:24]Br>C(O)(=O)C>[NH2:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:12])[C:10](=[O:13])[C:9]([CH3:15])([CH3:14])[N:8]=[C:7]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[Cl:22])[C:6]=2[C:23]=1[Br:24]

참가 물질

4

반응물 2

HCID 24408BromineHCID 205061787-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

생성물 1

HCID 205061367-amino-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one

시약·촉매·용매 1

HCID 176Acetic Acid용매2회

실험 절차

16 g (0.049 mol) of 7-amino-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one in 160 ml of glacial acetic acid are treated slowly while stirring with 8.5 g of bromine in 10 ml of glacial acetic acid. After 60 minutes at room temperature, the reaction mixture is concentrated and the residue is partitioned between aqueous ammonia and methylene chloride. The aqueous phase is extracted several times more with methylene chloride. The combined organic extracts are dried and evaporated. The crude product is purified on 500 g of silica gel with methylene chloride/ethyl acetate (5:1) as the elution agent. From ethyl acetate/ether there is obtained 7-amino-6-bromo-5-(o-chlorophenyl)-1,3-dihydro-1,3,3-trimethyl-2H-1,4-benzodiazepin-2-one of melting point 188°-189°.

후처리

  1. concentrationthe reaction mixture is concentrated
  2. customthe residue is partitioned between aqueous ammonia and methylene chloride
  3. extractionThe aqueous phase is extracted several times more with methylene chloride
  4. customThe combined organic extracts are dried
  5. customevaporated
  6. customThe crude product is purified on 500 g of silica gel with methylene chloride/ethyl acetate (5:1) as the elution agent

출처 및 근거

ORD 기록
ord-fb986af47cdf4980afdb94600b150631
출처 데이터셋
uspto-grants-1983_03
특허 번호
US04377522

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