1,1'-Carbonyldiimidazole → 3-[(4-Chlorophenyl)sulfonyl]-N-[2-(dimethylamino)ethyl]-1-pyrrolidinecarboxamide

HRID 236110Notes

Reaction equation

HRID 236110 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11][N:10]=[CH:9]1)(N1C=CN=C1)=[O:2].[CH3:13]NN(CC)NC.[Cl:20][C:21]1[CH:26]=[CH:25][C:24]([S:27]([CH:30]2[CH2:34][CH2:33][NH:32][CH2:31]2)(=[O:29])=[O:28])=[CH:23][CH:22]=1>O1CCCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([S:27]([CH:30]2[CH2:34][CH2:33][N:32]([C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:13])=[O:2])[CH2:31]2)(=[O:28])=[O:29])=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 136079763-[(4-Chlorophenyl)sulfonyl]pyrrolidineHCID 57041336N,N-Dimethylaminoethylamine

Product 1

HCID 136080093-[(4-Chlorophenyl)sulfonyl]-N-[2-(dimethylamino)ethyl]-1-pyrrolidinecarboxamideYield 51.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.00 g (0.0309 mole) of 1,1'-carbonyldiimidazole and 2.56 g (0.029 mole) of N,N-dimethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for about 1 hr. A solution of 5.99 g (0.0244 mole) of 3-[(4-chlorophenyl)sulfonyl]pyrrolidine (free base) in tetrahydrofuran was added and the solution was refluxed for 16 hr. The solvent was removed in vacuo and the resulting oil was dissolved in a mixture of 200 ml of diethyl ether and 20 ml of methylene chloride. The solution was extracted with one 150 ml portion of water. The ether phase was discarded. On standing at room temperature, the aqueous extract yielded a white precipitate. The precipitate was recrystallized from methylene chloride-diethyl ether to give 4.51 g (51.36%) of white crystals, m.p. 131°-132.5° C.

Workup

  1. temperaturethe solution was refluxed for 16 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in a mixture of 200 ml of diethyl ether and 20 ml of methylene chloride
  4. extractionThe solution was extracted with one 150 ml portion of water
  5. customOn standing at room temperature
  6. extractionthe aqueous extract
  7. customyielded a white precipitate
  8. customThe precipitate was recrystallized from methylene chloride-diethyl ether

Sources & evidence

ORD record
ord-061603b40d9b4e71908664aa403f50a0
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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