4-(Bromoacetyl)pyridine hydrobromide → HCID 178527846, compound

HRID 900733Notes

Reaction equation

HRID 900733 reaction equation
[C:1](=[S:4])([S-:3])[NH2:2].[NH4+].Br.Br[CH2:8][C:9]([C:11]1[CH:16]=[CH:15][N:14]=[CH:13][CH:12]=1)=O>C(O)C>[N:14]1[CH:15]=[CH:16][C:11]([C:9]2[N:2]=[C:1]([SH:3])[S:4][CH:8]=2)=[CH:12][CH:13]=1

Participants

4

Reactant 2

HCID 27762394-(Bromoacetyl)pyridine hydrobromideHCID 11083854Ammonium dithiocarbamate

Product 1

HCID 178527846HCID 178527846, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ammonium dithiocarbamate (0.444 g, 4.03 mmol) was added to 2-bromo-1-(4-pyridinyl)-1-ethanone hydrobromide (1.03 g, 3.67 mmol) in ethanol (10 ml and stirring continued at room temperature for 18 hr. The solid was filtered and re-crystallized from methanol to give 4-pyridin-4-yl-thiazole-2-thiol. This thiol (272 mg, 1.39 mmol) was then coupled with N1-3-chlorophenyl)-2-chloroacetamide (284 mg, 1.39 mmol) as described in earlier examples, in acetonitrile in the presence of triethylamine (0.580 ml, 4.2 mmol) to afford crude product. This was purified by reverse phase HPLC to afford N-(3-Chloro-phenyl)-2-(4-pyridin-4-yl-thiazol-2-ylsulfanyl)-acetamide. MS (ES) 363 (M+H)+

Workup

  1. filtrationThe solid was filtered
  2. customre-crystallized from methanol

Sources & evidence

ORD record
ord-6c0adef5edce45e281fdb6bd63ab41f9
Source dataset
uspto-grants-2008_04
Patent number
US07361669B2

Reaction notes

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