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

HRID 1939178Notes

Reaction equation

HRID 1939178 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.[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([C:25](Cl)=[O:26])=[CH:23][CH:22]=1)([O-:20])=[O:19]>ClCCl>[N+:18]([C:21]1[CH:22]=[CH:23][C:24]([C:25]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[O:26])=[CH:28][CH:29]=1)([O-:20])=[O:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 85024-Nitrobenzoyl chlorideHCID 118049715,6,7,8-Tetrahydro-4H-thieno[3,2-B]azepine

Product 1

HCID 153693984-(4-Nitrobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 10.71 g of 5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine and 19.4 ml of triethylamine amine in 150 ml of dichloromethane under argon is added in small portions 4-nitrobenzoyl chloride (exothermic). The mixture is stirred for 3 hours at 25° C. and then washed with water, sodium bicarbonate solution, brine and dried (Na2SO4). The solvent is removed, the residue dried under vacuum and recrystallized by dissolving in hot ethyl acetate and diluting with hexane. Chilling overnight and filtering gives 16 g of light brown crystals, m.p. 141°-142° C.

Workup

  1. washwashed with water, sodium bicarbonate solution, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. customthe residue dried under vacuum
  5. customrecrystallized
  6. dissolutionby dissolving in hot ethyl acetate
  7. additiondiluting with hexane
  8. temperatureChilling overnight
  9. filtrationfiltering

Sources & evidence

ORD record
ord-1d3136729df34c60a26a4eb2c9a64490
Source dataset
uspto-grants-1997_12
Patent number
US05696112

Reaction notes

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