Thioacetamide → (2-Methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulen-6-yl)-phenyl-methanone

HRID 220786Notes

Reaction equation

HRID 220786 reaction equation
[C:1]([N:9]1[CH2:15][CH2:14][CH:13](Br)[C:12](=O)[C:11]2[CH:18]=[CH:19][CH:20]=[CH:21][C:10]1=2)(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22]([NH2:25])(=[S:24])[CH3:23]>C(O)C>[CH3:23][C:22]1[S:24][C:13]2[CH2:14][CH2:15][N:9]([C:1]([C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[O:8])[C:10]3[CH:21]=[CH:20][CH:19]=[CH:18][C:11]=3[C:12]=2[N:25]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 231123501-Benzoyl-4-bromo-1,2,3,4-tetrahydro-benzo[b]azepin-5-one

Product 1

HCID 23112323(2-Methyl-4,5-dihydro-3-thia-1,6-diaza-benzo[e]azulen-6-yl)-phenyl-methanoneYield 70%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 1-benzoyl-4-bromo-1,2,3,4-tetrahydrobenzo[b]azepin-5-one (11.0 g, 2.9 mmol) from Example E5.7 in ethanol (50 ml) was added thioacetamide (0.75 g, 10 mmol). The solution was stirred for 16 h. The resultant suspension was reduced in volume by evaporation and cooled. The precipitate was collected by filtration and the solid was washed with cold ethanol and dried to yield the title compound as a white solid (0.65 g, 70%).

Workup

  1. customThe resultant suspension was reduced in volume by evaporation
  2. temperaturecooled
  3. filtrationThe precipitate was collected by filtration
  4. washthe solid was washed with cold ethanol
  5. customdried

Sources & evidence

ORD record
ord-aabd500b712c4d4086ad85fec0c06704
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Reaction notes

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