Ethyl thiooxamate → Ethyl 4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

HRID 2038360Notes

Reaction equation

HRID 2038360 reaction equation
Br[CH2:2][C:3]([C:5]1[CH:10]=[CH:9][C:8]([F:11])=[C:7]([Cl:12])[CH:6]=1)=O.[NH2:13][C:14](=[S:20])[C:15]([O:17][CH2:18][CH3:19])=[O:16]>C(O)C>[Cl:12][C:7]1[CH:6]=[C:5]([C:3]2[N:13]=[C:14]([C:15]([O:17][CH2:18][CH3:19])=[O:16])[S:20][CH:2]=2)[CH:10]=[CH:9][C:8]=1[F:11]

Participants

4

Reactant 2

HCID 2733398Ethyl thiooxamateHCID 27827852-Bromo-3'-chloro-4'-fluoroacetophenone

Product 1

HCID 61385370Ethyl 4-(3-chloro-4-fluorophenyl)-1,3-thiazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

1.35 g of the compound from Example 1A having a purity of 68% (5.37 mmol) are heated under reflux in 25 ml of ethanol, a solution of 0.72 g (5.37 mmol) of ethyl amino(thioxo)acetate and 10 ml of ethanol is added dropwise and the mixture is heated under reflux for 18 hours. The reaction mixture is concentrated and the residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1), and 1.94 g of the title compound having a purity of 57% (100% of theory) are obtained.

Workup

  1. temperatureare heated
  2. temperaturethe mixture is heated
  3. temperatureunder reflux for 18 hours
  4. concentrationThe reaction mixture is concentrated
  5. customthe residue is purified by flash chromatography (mobile phase: cyclohexane/ethyl acetate 10:1), and 1.94 g of the title compound
  6. customare obtained

Sources & evidence

ORD record
ord-7dbe9f8e65c546799279de297ac7ce8d
Source dataset
uspto-grants-2013_11
Patent number
US08575357B2

Reaction notes

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