Methyl 2-chloroacetoacetate → Methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate

HRID 1710797Notes

Reaction equation

HRID 1710797 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12](=[S:14])[NH2:13])=[CH:8][CH:7]=1.[CH3:15][O:16][C:17](=[O:23])[CH:18](Cl)[C:19]([CH3:21])=O>CO.ClCCl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[S:14][C:18]([C:17]([O:16][CH3:15])=[O:23])=[C:19]([CH3:21])[N:13]=2)=[CH:8][CH:7]=1

Participants

5

Reactant 2

HCID 107332Methyl 2-chloroacetoacetateHCID 594574624-(3-Chloropropoxy)benzenecarbothioamide

Product 1

HCID 59457477Methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylateYield 100%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
70 °C

Procedure

A mixture of 4-(3-chloropropoxy)benzenecarbothioamide ax71 (34.67 mmol, 1 eq, 7.96 g), and 2-chloroacetoacetic acid methyl ester (34.67 mmol, 1 eq, 5.2 g) in methanol is stirred at 70° C. for 2 hours. The reaction mixture is then poured into a sealed tube and stirred at 100° C. for 3 hours. The mixture is taken up in dichloromethane and washed with water then dried over magnesium sulfate. The solvent is removed under reduced pressure to give 11.8 g of methyl 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-thiazole-5-carboxylate i105. The product is used as such in the next step.

Workup

  1. additionThe reaction mixture is then poured into a sealed tube
  2. stirringstirred at 100° C. for 3 hours
  3. washwashed with water
  4. dry with materialthen dried over magnesium sulfate
  5. customThe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-9624aa445ed34b9eb8480f8a9fd7c570
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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