Thioacetamide → 5,6-Dihydro-2-methyl-6-(4-nitrobenzoyl)-4H-thiazolo[5,4-d] [1]benzazepine

HRID 362373Notes

Reaction equation

HRID 362373 reaction equation
Br[CH:2]1[C:8](=O)[C:7]2[CH:10]=[CH:11][CH:12]=[CH:13][C:6]=2[N:5]([C:14](=[O:24])[C:15]2[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=2)[CH2:4][CH2:3]1.[C:25]([NH2:28])(=[S:27])[CH3:26]>C(O)C>[CH3:26][C:25]1[S:27][C:2]2[CH2:3][CH2:4][N:5]([C:14](=[O:24])[C:15]3[CH:20]=[CH:19][C:18]([N+:21]([O-:23])=[O:22])=[CH:17][CH:16]=3)[C:6]3[CH:13]=[CH:12][CH:11]=[CH:10][C:7]=3[C:8]=2[N:28]=1

Participants

4

Reactant 2

HCID 2723949ThioacetamideHCID 540926514-bromo-1-(4-nitrobenzoyl)-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

Product 1

HCID 867515725,6-Dihydro-2-methyl-6-(4-nitrobenzoyl)-4H-thiazolo[5,4-d] [1]benzazepineYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 1.19 g of 4-bromo-1,2,3,4-tetrahydro-1-(4-nitrobenzoyl)-5H-1-benzazepin-5-one and 0.230 g of thioacetamide in 4 ml of ethyl alcohol is refluxed under argon for 18 hours. The volatiles are evaporated in vacuo to a residue which is partitioned between CHCl3 and 10% NaHCO3. The organic layer is separated and washed twice with water. The organic layer is separated, dried (MgSO4) and evaporated in vacuo to give 1.08 g of yellow foam which is purified is by flash chromatography on silica by elution with 4% ethyl acetate in methylene chloride to give 560 mg of the desired product as pale yellow foam.

Workup

  1. temperatureis refluxed under argon for 18 hours
  2. customThe volatiles are evaporated in vacuo to a residue which
  3. customis partitioned between CHCl3 and 10% NaHCO3
  4. customThe organic layer is separated
  5. washwashed twice with water
  6. customThe organic layer is separated
  7. dry with materialdried (MgSO4)
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-19c625208d9d40b3ae6a3ca2b7e5f4ea
Source dataset
uspto-grants-1999_02
Patent number
US05869483

Reaction notes

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