Bromine → 7-bromo-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno(2,3-e)(1,4)diazepin-2-one

HRID 1816515노트

반응식

HRID 1816515 반응식
[NH2:1][CH2:2][C:3]([NH:5][C:6]1[S:7][CH:8]=[CH:9][C:10]=1[C:11](=O)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=1[Cl:18])=[O:4].NC1SC=CC=1C(=O)C1C=CC=CC=1Cl.[Br:35]CC(Br)=O.BrBr>N.N1C=CC=CC=1.C(O)(=O)C.C(O)CCC>[Br:35][C:8]1[S:7][C:6]2[NH:5][C:3](=[O:4])[CH2:2][N:1]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[Cl:18])[C:10]=2[CH:9]=1

참가 물질

9

반응물 4

HCID 24408BromineHCID 61147Bromoacetyl bromideHCID 8271262-AMINO-3-(2-CHLOROBENZOYL)THIOPHENEHCID 113808702-amino-N-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide

생성물 1

HCID 1354301237-bromo-5-(2-chlorophenyl)-1,3-dihydro-2H-thieno(2,3-e)(1,4)diazepin-2-one

시약·촉매·용매 4

HCID 176Acetic Acid용매HCID 222Ammonia용매HCID 2631-Butanol용매HCID 1049Pyridine용매

실험 절차

220 g (0.746 mol) of 2-amino-N-[3-(2-chlorobenzoyl)thiophen-2-yl]acetamide (prepared by reacting 2-amino-3-(2-chlorobenzoyl)thiophene with bromoacetylbromide and subsequently piping in gaseous ammonia) are added at 110° C. to a mixture of 1.8 l of n-butanol and 150 ml of glacial acetic acid. The mixture is refluxed for 1 hour, cooled to ambient temperature and 330 ml of pyridine and 57 ml (178.8 g, 1.12 mol) of bromine are added with cooling. Then the mixture is stirred for another 0.5 to 2 hours, cooled to 5 to 10° C. and stirred for a further 2 hours at this temperature. The product that crystallises out is isolated by filtration, washed with 50% ethanol and dried overnight in vacuo at 60° C.

후처리

  1. temperatureThe mixture is refluxed for 1 hour
  2. temperaturewith cooling
  3. temperaturecooled to 5 to 10° C.
  4. stirringstirred for a further 2 hours at this temperature
  5. customThe product that crystallises out
  6. customis isolated by filtration
  7. washwashed with 50% ethanol
  8. customdried overnight in vacuo at 60° C.

출처 및 근거

ORD 기록
ord-049ca737ef694f21b653a54994f936b8
출처 데이터셋
uspto-grants-2005_04
특허 번호
US06884886B2

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