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

HRID 1816515Notes

Reaction equation

HRID 1816515 reaction equation
[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

Participants

9

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 4

HCID 176Acetic AcidSolventHCID 222AmmoniaSolventHCID 2631-ButanolSolventHCID 1049PyridineSolvent

Procedure

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.

Workup

  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.

Sources & evidence

ORD record
ord-049ca737ef694f21b653a54994f936b8
Source dataset
uspto-grants-2005_04
Patent number
US06884886B2

Reaction notes

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