Triethylamine → 4-(2-Chloro-4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

HRID 1939188Notes

Reaction equation

HRID 1939188 reaction equation
[S:1]1[C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][NH:5][C:4]=2[CH:3]=[CH:2]1.C(N(CC)CC)C.[Cl:18][C:19]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:20]=1[C:21](Cl)=[O:22]>ClCCl>[Cl:18][C:19]1[CH:27]=[C:26]([N+:28]([O-:30])=[O:29])[CH:25]=[CH:24][C:20]=1[C:21]([N:5]1[CH2:6][CH2:7][CH2:8][CH2:9][C:10]2[S:1][CH:2]=[CH:3][C:4]1=2)=[O:22]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 81522Benzoyl chloride, 2-chloro-4-nitro-HCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Product 1

HCID 196990734-(2-Chloro-4-nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepineYield 73.7%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution of 15.0 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine in 150 ml of dichloromethane cooled to 0° C. is added 27.2 ml of triethylamine. After stirring 5 minutes, a solution of 28.0 g of 2-chloro-4-nitrobenzoyl chloride in 140 ml of dichloromethane is added slowly. The solution is stirred at room temperature overnight, diluted with 450 ml of dichloromethane and the solution washed with 200 ml each of water, 2N citric acid, 1M sodium bicarbonate and brine. The organic layer is dried over N2SO4, filtered through a thin pad of hydrated magnesium silicate and the filtrate concentrated under vacuum. The residue is crystallized from ethyl acetate to give 24.3 g of off-white crystals, m.p. 131°-134° C.

Workup

  1. stirringThe solution is stirred at room temperature overnight
  2. washthe solution washed with 200 ml each of water, 2N citric acid, 1M sodium bicarbonate and brine
  3. customThe organic layer is dried over N2SO4
  4. filtrationfiltered through a thin pad of hydrated magnesium silicate
  5. concentrationthe filtrate concentrated under vacuum
  6. customThe residue is crystallized from ethyl acetate

Sources & evidence

ORD record
ord-7620ec0f394e45ad83f2d7e17957d504
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

Loading…