Thiophene → HCID 10514014, compound

HRID 236998Notes

Reaction equation

HRID 236998 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][C:9]([OH:11])=O)=[CH:4][CH:3]=1.[S:12]1[CH:16]=[CH:15][CH:14]=[CH:13]1.FC(F)(F)C(OC(=O)C(F)(F)F)=O.C(=O)([O-])[O-].[Na+].[Na+]>O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:8][C:9]([C:13]2[S:12][CH:16]=[CH:15][CH:14]=2)=[O:11])=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 8030ThiopheneHCID 9845Trifluoroacetic anhydrideHCID 10340Sodium CarbonateHCID 15880(4-Chlorophenyl)acetic acid

Product 1

HCID 10514014HCID 10514014, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 85.3 g of p-chlorophenylacetic acid and 200 ml of thiophene was stirred at 40° C. as 105 g of trifluoroacetic anhydride was added. The mixture was then refluxed for 4 hrs. It was poured into ice and water and made basic with sodium carbonate. The mixture was extracted with dichloromethane, dried over potassium carbonate and concentrated. The crude yield was 126.4 g. This was recrystallized from 300 ml of methanol to give 103 g, m.p. 98°-99° C.

Workup

  1. additionwas added
  2. temperatureThe mixture was then refluxed for 4 hrs
  3. extractionThe mixture was extracted with dichloromethane
  4. dry with materialdried over potassium carbonate
  5. concentrationconcentrated
  6. customThis was recrystallized from 300 ml of methanol
  7. customto give 103 g, m.p. 98°-99° C.

Sources & evidence

ORD record
ord-dab0fa3ab1304e4980c4414ac9dd6baa
Source dataset
uspto-grants-1979_06
Patent number
US04159338

Reaction notes

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