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

HRID 504309Notes

Reaction equation

HRID 504309 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 triturated 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. customThe residue was triturated with ether
  6. filtrationfollowed by filtration
  7. customto afford the product

Sources & evidence

ORD record
ord-32c4e090cfec47978763f52357f80375
Source dataset
uspto-grants-2010_08
Patent number
US07776874B2

Reaction notes

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