Ethanol → HCID 12437469, compound

HRID 2177214Notes

Reaction equation

HRID 2177214 reaction equation
S(Cl)(Cl)=O.[Cl:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[C:16]([C:17]([OH:19])=[O:18])=[CH:15][S:14][N:13]=2)=[CH:8][CH:7]=1.[CH2:20](O)[CH3:21]>>[Cl:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[C:16]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:15][S:14][N:13]=2)=[CH:10][CH:11]=1

Participants

4

Reactant 3

HCID 702EthanolHCID 24386Thionyl ChlorideHCID 12437453HCID 12437453, compound

Product 1

HCID 12437469HCID 12437469, compound

Conditions

Temperature
90 °C

Procedure

Into a 50-mL round-bottom flask, was placed ethanol (10 mL), thionyl chloride (440 mg, 3.70 mmol, 1.00 equiv), 3-(4-chlorophenyl)-1,2-thiazole-4-carboxylic acid (860 mg, 3.69 mmol, 1.00 equiv). The resulting solution was stirred for 6 h at 90° C. in an oil bath. The resulting mixture was concentrated under vacuum and taken up in 150 mL of dichloromethane, washed with 1×30 mL of brine. The solution was dried over anhydrous sodium sulfate and concentrated under vacuum. This resulted in 0.72 g (75%) of ethyl 3-(4-chlorophenyl)-1,2-thiazole-4-carboxylate as brown oil.

Workup

  1. customInto a 50-mL round-bottom flask, was placed
  2. concentrationThe resulting mixture was concentrated under vacuum
  3. washwashed with 1×30 mL of brine
  4. dry with materialThe solution was dried over anhydrous sodium sulfate
  5. concentrationconcentrated under vacuum
  6. customThis resulted in 0.72 g (75%) of ethyl 3-(4-chlorophenyl)-1,2-thiazole-4-carboxylate as brown oil

Sources & evidence

ORD record
ord-ecc404debbb14c29b9f44f8624b98715
Source dataset
uspto-grants-2015_06
Patent number
US09067898B1

Reaction notes

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