Methane → Methyl 2-aminothiazole-5-carboxylate

HRID 736434Notes

Reaction equation

HRID 736434 reaction equation
[CH3:1][O:2][C:3](=[O:8])[CH:4](Cl)[CH:5]=O.[NH2:9][C:10]([NH2:12])=[S:11].C>O>[CH3:1][O:2][C:3]([C:4]1[S:11][C:10]([NH2:12])=[N:9][CH:5]=1)=[O:8]

Participants

5

Reactant 3

HCID 297MethaneHCID 2723790ThioureaHCID 14355182Methyl 2-chloro-3-oxopropanoate

Product 1

HCID 238005Methyl 2-aminothiazole-5-carboxylateYield 44.2%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2.4 g of 2-chloro-3-oxo-propionic acid methyl ester (7-2), water 20 ml and 1.75 g of thiourea was refluxed for 2 hours. The mixture was cooled to room temperature and 0.25 g of norit was added and filtered. A solution of 2.5N sodium hydroxide was added to the filtrate until neutral pH. The filtration yielded 1.23 g (44%) of 2-aminothiazole-5-carboxylic acid methyl ester (7-3).

Workup

  1. temperaturewas refluxed for 2 hours
  2. filtrationfiltered
  3. additionA solution of 2.5N sodium hydroxide was added to the filtrate until neutral pH
  4. filtrationThe filtration

Sources & evidence

ORD record
ord-750a5a63b9f047e3ba0d4882c5e3e973
Source dataset
uspto-grants-2009_09
Patent number
US07595334B2

Reaction notes

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