Sodium Carbonate → Ethyl 2-amino-4-methylthiazole-5-carboxylate

HRID 1919591Notes

Reaction equation

HRID 1919591 reaction equation
Cl[CH:2]([C:8]([CH3:10])=O)[C:3]([O:5][CH2:6][CH3:7])=[O:4].[NH2:11][C:12]([NH2:14])=[S:13].C([O-])([O-])=O.[Na+].[Na+]>CC#N.C1COCC1>[NH2:14][C:12]1[S:13][C:2]([C:3]([O:5][CH2:6][CH3:7])=[O:4])=[C:8]([CH3:10])[N:11]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 11858Ethyl 2-chloroacetoacetateHCID 2723790Thiourea

Product 1

HCID 343747Ethyl 2-amino-4-methylthiazole-5-carboxylateYield 38%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
120 °C

Procedure

To a stirred solution of ethyl 2-chloroacetoacetate (6.0 mL, 43.35 mmol) in MeCN (24 mL) and THF (6 mL) was added thiourea (3.0 g, 39.41 mmol) and Na2CO3 (0.417 g, 39.41 mmol). The reaction mixture was heated at 120° C. under microwave irradiation for 30 minutes, cooled to r.t., partitioned between EtOAc and water, and the organic fraction was dried (MgSO4), filtered and concentrated in vacuo to give the title compound (2.76 g, 38%) as a cream solid. δH (CDCl3) 5.47 (2H, br. s), 4.27 (2H, q, J 7.2 Hz), 2.53 (3H, s), 1.33 (3H, t, J 7.2 Hz). MS (ES+) 187.0 (M+H)+.

Workup

  1. temperaturecooled to r.t.
  2. custompartitioned between EtOAc and water
  3. dry with materialthe organic fraction was dried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-5f2ee8fb55a84348840e9e59884451a3
Source dataset
uspto-grants-2012_05
Patent number
US08168634B2

Reaction notes

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