Thiourea → Methyl 2-amino-4-(methoxymethyl)thiazole-5-carboxylate

HRID 908630Notes

Reaction equation

HRID 908630 reaction equation
[CH3:1][O:2][C:3](=[O:11])[CH:4](Br)[C:5](=O)[CH2:6][O:7][CH3:8].[NH2:12][C:13]([NH2:15])=[S:14]>C(O)C>[CH3:1][O:2][C:3]([C:4]1[S:14][C:13]([NH2:15])=[N:12][C:5]=1[CH2:6][O:7][CH3:8])=[O:11]

Participants

4

Reactant 2

HCID 2723790ThioureaHCID 53423683Methyl 2-bromo-4-methoxy-3-oxobutanoate

Product 1

HCID 25220423Methyl 2-amino-4-(methoxymethyl)thiazole-5-carboxylateYield 54%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of the crude product (about 30 mmol) obtained in Step 1 and thiourea (2.28 g) in ethanol (60 ml) was heated under reflux overnight. After cooling to room temperature, the reaction mixture was partitioned by adding ethyl acetate and water. The organic layer was washed successively with water and saturated brine, dried over anhydrous magnesium sulfate, filtrated, and concentrated under reduced pressure. Then, suitable amounts of isopropanol, chloroform, ethyl acetate and diisopropyl ether were added, and the mixture was stirred at room temperature for 30 min. The precipitated crystals were collected by filtration and dried to give the title compound (3.27 g).

Workup

  1. temperatureunder reflux overnight
  2. customthe reaction mixture was partitioned
  3. additionby adding ethyl acetate and water
  4. washThe organic layer was washed successively with water and saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. filtrationfiltrated
  7. concentrationconcentrated under reduced pressure
  8. additionThen, suitable amounts of isopropanol, chloroform, ethyl acetate and diisopropyl ether were added
  9. filtrationThe precipitated crystals were collected by filtration
  10. customdried

Sources & evidence

ORD record
ord-4c3ca7b09f8d428e9208b2aef89a2616
Source dataset
uspto-grants-2011_09
Patent number
US08017612B2

Reaction notes

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