Thiourea → Ethyl 2-amino-5-(3-chloropropyl)thiazole-4-carboxylate

HRID 2178228Notes

Reaction equation

HRID 2178228 reaction equation
Br[CH:2]([CH2:10][CH2:11][CH2:12][Cl:13])[C:3](=O)[C:4]([O:6][CH2:7][CH3:8])=[O:5].[NH2:14][C:15]([NH2:17])=[S:16]>CC(C)=O>[NH2:17][C:15]1[S:16][C:2]([CH2:10][CH2:11][CH2:12][Cl:13])=[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])[N:14]=1

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 59418695Ethyl 3-bromo-6-chloro-2-oxohexanoate

Product 1

HCID 59418686Ethyl 2-amino-5-(3-chloropropyl)thiazole-4-carboxylateYield 93%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

To a solution of ethyl 3-bromo-6-chloro-2-oxohexanoate (23A) (0.845 g, 3.11 mmol) in acetone (6 mL) was added thiourea (0.284 g, 3.73 mmol) and refluxed overnight. The reaction mixture was concentrated under reduced pressure. EtOAc and hexanes in a ratio of 1:9 was added and stirred for 1 hour. Added acetone to dissolve material and concentrated under reduced pressure to give 0.718 g (93%) of the desired product ethyl 2-amino-5-(3-chloropropyl)thiazole-4-carboxylate (23B): LC/MS (APCI): m/z 249.5 (M+H).

Workup

  1. temperaturerefluxed overnight
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionEtOAc and hexanes in a ratio of 1:9 was added
  4. dissolutionAdded acetone to dissolve material
  5. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-5b1d218997914c5f9dfd7b9a18329f34
Source dataset
uspto-grants-2015_06
Patent number
US09067928B2

Reaction notes

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