Triethylamine → HCID 21467152, compound

HRID 2255983Notes

Reaction equation

HRID 2255983 reaction equation
[Cl:1][C:2]1[S:11][C:10]2[CH2:9][CH2:8][CH2:7][CH2:6][N:5]([C:12](=[O:20])[C:13]3[CH:18]=[CH:17][C:16]([NH2:19])=[CH:15][CH:14]=3)[C:4]=2[CH:3]=1.C(N(CC)CC)C.[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31](Cl)=[O:32]>ClCCl>[Cl:28][C:29]1[CH:37]=[C:36]([Cl:38])[CH:35]=[CH:34][C:30]=1[C:31]([NH:19][C:16]1[CH:15]=[CH:14][C:13]([C:12]([N:5]2[CH2:6][CH2:7][CH2:8][CH2:9][C:10]3[S:11][C:2]([Cl:1])=[CH:3][C:4]2=3)=[O:20])=[CH:18][CH:17]=1)=[O:32]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 666452,4-Dichlorobenzoyl chlorideHCID 21467127(4-Aminophenyl)(2-chloro-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepin-4-yl)methanone

Product 1

HCID 21467152HCID 21467152, compoundYield 82.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a cooled (ice bath) solution of 0.245 g (0.8 mmol) of 2-chloro-4-(4-aminobenzoyl)-5,6,7,8-tetrahydro-4H-thieno[3,2-b]azepine and 167 μl (1.2 mmol) of triethylamine in 5 ml of dichloromethane is added 140 μl (1 mmol) of 2,4-dichlorobenzoyl chloride. The solution is stirred under argon at room temperature overnight and diluted with 60 ml of dichloromethane. The mixture is washed with 20 ml each of 2N-citric acid, H2O, 1M NaHCO3, brine and dried (Na2SO4). The solvent is removed and the residue crystallized from ethyl acetate-hexane to give 0.315 g of white crystals, m.p. 187°-189° C.

Workup

  1. washThe mixture is washed with 20 ml each of 2N-citric acid, H2O, 1M NaHCO3, brine
  2. dry with materialdried (Na2SO4)
  3. customThe solvent is removed
  4. customthe residue crystallized from ethyl acetate-hexane

Sources & evidence

ORD record
ord-12e34504bfaa4e92bfdaefab5c1047f3
Source dataset
uspto-grants-1997_08
Patent number
US05654297

Reaction notes

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