2-(4-chlorophenyl)ethanethioamide → HCID 69448752, compound

HRID 1593018Notes

Reaction equation

HRID 1593018 reaction equation
Br[CH2:2][C:3]([CH:5]1[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:7][CH2:6]1)=O.[Cl:17][C:18]1[CH:23]=[CH:22][C:21]([CH2:24][C:25](=[S:27])[NH2:26])=[CH:20][CH:19]=1>C(O)C>[Cl:17][C:18]1[CH:19]=[CH:20][C:21]([CH2:24][C:25]2[S:27][CH:2]=[C:3]([CH:5]3[CH2:10][CH2:9][N:8]([C:11]([O:13][CH2:14][CH:15]=[CH2:16])=[O:12])[CH2:7][CH2:6]3)[N:26]=2)=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 27348272-(4-chlorophenyl)ethanethioamideHCID 18623152Prop-2-en-1-yl 4-(bromoacetyl)piperidine-1-carboxylate

Product 1

HCID 69448752HCID 69448752, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of allyl 4-(bromoacetyl)piperidine-1-carboxylate (547 mg) and 2-(4-chlorophenyl)ethanethioamide (366 mg) in ethanol (15 ml) was refluxed for 5 hours. The reaction mixture was evaporated to dryness and the residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98) to give allyl 4-[2-(4-chlorobenzyl)-1,3-thiazol-4-yl]piperidine-1-carboxylate. Yield 698 mg. NMR (CDCl3): 1.65 (m, 2H), 2.25 (m, 2H), 2.95 (m, 2H), 3.2 (m, 1H), 4.3 (m, 2H), 4.55 (m, 4H), 5.3 (m, 2H), 6.0 (m, 1H), 6.95 (s, 1H), 7.35 (m, 4H).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customThe reaction mixture was evaporated to dryness
  3. customthe residue was purified by chromatography on silica eluting with methanol/dichloromethane (2:98)

Sources & evidence

ORD record
ord-09d090415d694169962be4fb7eaf3062
Source dataset
uspto-grants-2007_11
Patent number
US07294636B2

Reaction notes

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