Carbon Dioxide → HCID 15022347, compound

HRID 1770321Notes

Reaction equation

HRID 1770321 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]>O1CCCC1>[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 tetrahydrofuran, the solution is cooled to -70° C. and n-butyllithium (0.13 mol, 1.6N solution in n-hexane) is added. After 30 minutes, carbon dioxide gas is passed in until the solution is saturated, and the solution is allowed to warm up slowly to room temperature. It is worked up by evaporating to dryness, taking up the solution residue n a mixture of water, sodium hydroxide solution and ethyl acetate, separating the phases and acidifying the aqueous phase with hydrochloric acid. The carboxylic acid is precipitated. Yield: 13.6 g, 78%, mp. 208° to 210° C.

Workup

  1. temperatureto warm up slowly to room temperature
  2. customby evaporating to dryness
  3. additiona mixture of water, sodium hydroxide solution and ethyl acetate
  4. customseparating the phases
  5. customThe carboxylic acid is precipitated

Sources & evidence

ORD record
ord-5b571bf9dfc741bd9a85e328947bcf45
Source dataset
uspto-grants-1995_01
Patent number
US05386036

Reaction notes

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