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

HRID 862990Notes

Reaction equation

HRID 862990 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)=[CH:23][CH:22]=1)([O-:20])=[O:19]>ClCCl>[N+:18]([C:21]1[CH:29]=[CH:28][C:24]([CH2:25][N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:1][CH:2]=[CH:3][C:4]2=3)=[CH:23][CH:22]=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 196990844-(4-Nitrobenzyl)-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-tetra-hydro-4H-thieno[3,2-b]azepine and 19.4 ml of triethylamine 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-4d47a736f47e408194dbdd30ab0b92b2
Source dataset
uspto-grants-1998_02
Patent number
US05719278

Reaction notes

Loading…