Carbon Dioxide → HCID 15022347, compound

HRID 256522Notes

Reaction equation

HRID 256522 reaction equation
[Cl:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)=[O:8])=[CH:4][S:5][CH:6]=1.C([Li])CCC.[C:21](=[O:23])=[O:22]>C1COCC1>[Cl:1][C:2]1[C:3]([C:7]([NH:9][C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][CH:15]=2)=[O:8])=[C:4]([C:21]([OH:23])=[O:22])[S:5][CH:6]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 15022346HCID 15022346, compoundHCID 178418339Butyllithium

Product 1

HCID 15022347HCID 15022347, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-70 °C

Procedure

4-Chlorothiophene-3-carboxanilide (14.6 g, 0.061 mol) is dissolved in 450 ml of THF and the solution is cooled to -70° C.; n-butyllithium (0.13 mol, 1.6N solution in n-hexane) is then added. After 30 minutes, carbon dioxide is gassed in until the solution was saturated, and the solution is allowed to heat up slowly to room temperature. It is then concentrated to dryness, the solid residue is taken up in a mixture of water, sodium hydroxide solution and ethyl acetate, the phases are separated and the aqueous phase is acidified with hydrochloric acid, thus precipitating the carboxylic acid. Yield: 13.5 g, 78%; m.p. 208°-210° C. (active ingredient no. 2.008).

Workup

  1. temperatureto heat up slowly to room temperature
  2. concentrationIt is then concentrated to dryness
  3. additionthe solid residue is taken up in a mixture of water, sodium hydroxide solution and ethyl acetate
  4. customthe phases are separated
  5. customthus precipitating the carboxylic acid

Sources & evidence

ORD record
ord-a98bb1d9ed8b43029bbe045dea276166
Source dataset
uspto-grants-1993_11
Patent number
US05258357

Reaction notes

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