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

HRID 1816515ノート

反応式

HRID 1816515 の反応式
[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

参加物

9

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 4

HCID 176Acetic Acid溶媒HCID 222Ammonia溶媒HCID 2631-Butanol溶媒HCID 1049Pyridine溶媒

実験手順

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.

後処理

  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.

出典と根拠

ORDレコード
ord-049ca737ef694f21b653a54994f936b8
出典データセット
uspto-grants-2005_04
特許番号
US06884886B2

反応ノート

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