Methyl 4-chloroacetoacetate → (2-Amino-thiazol-4-yl)-acetic acid methyl ester hydrochloride

HRID 1457530Notes

Reaction equation

HRID 1457530 reaction equation
[Cl:1][CH2:2][C:3](=O)[CH2:4][C:5]([O:7][CH3:8])=[O:6].[NH2:10][C:11]([NH2:13])=[S:12]>C1COCC1>[ClH:1].[NH2:13][C:11]1[S:12][CH:2]=[C:3]([CH2:4][C:5]([O:7][CH3:8])=[O:6])[N:10]=1

Participants

4

Reactant 2

HCID 36240Methyl 4-chloroacetoacetateHCID 2723790Thiourea

Product 1

HCID 6602854(2-Amino-thiazol-4-yl)-acetic acid methyl ester hydrochlorideYield 90%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of methyl 4-chloro-acetoacetate (4.0 g, 27 mmol) in 50 mL of THF was added thiourea (2.0 g, 27 mmol) and the resulting suspension was stirred at reflux for 5 h. The mixture was allowed to cool to room temperature. The white solid was filtered off and washed with ether to afford 5.0 g (90%) of the title compound. 1H NMR (D2O) δ 6.6 (broad s, 1H), 3.7 (broad s, 2H), 3.6 (broad s, 3H). MS (NH3 --CI) 173 (M+H)+ (100%).

Workup

  1. temperatureat reflux for 5 h
  2. filtrationThe white solid was filtered off
  3. washwashed with ether

Sources & evidence

ORD record
ord-8e6cc127ed63484c9074aa73e00de5c1
Source dataset
uspto-grants-1998_12
Patent number
US05849693

Reaction notes

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