Thiourea → Methyl1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate

HRID 557847Notes

Reaction equation

HRID 557847 reaction equation
Cl[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]2)=[CH:7][CH:6]=1)=O.[NH2:18][C:19]([NH2:21])=[S:20]>C(O)C.C(OCC)(=O)C>[NH2:21][C:19]1[S:20][CH:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([C:11]3([C:14]([O:16][CH3:17])=[O:15])[CH2:13][CH2:12]3)=[CH:7][CH:6]=2)[N:18]=1

Participants

5

Reactant 2

HCID 2723790ThioureaHCID 86602275Methyl1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate

Product 1

HCID 86602276Methyl1-[4-(2-amino-1,3-thiazol-4-yl)phenyl]cyclopropanecarboxylate

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of methyl 1-[4-(chloroacetyl)phenyl]cyclopropanecarboxylate (0.30 g, 1.2 mmol) and thiourea (0.18 g, 2.4 mmol) in ethanol (5.0 ml) was refluxed overnight. The reaction mixture was diluted with ethyl acetate and washed with saturated NaHCO3 and brine successively; then dried; and then concentrated. The residue was tritrurated with ether followed by filtration to afford the product. LC-MS: 275.1 (M+H)+.

Workup

  1. temperaturewas refluxed overnight
  2. washwashed with saturated NaHCO3 and brine successively
  3. customthen dried
  4. concentrationand then concentrated
  5. filtrationfollowed by filtration
  6. customto afford the product

Sources & evidence

ORD record
ord-405f8e0f86b14b8c9acf58fa43bf82ce
Source dataset
uspto-grants-2011_11
Patent number
US08058288B2

Reaction notes

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