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

HRID 236107Notes

Reaction equation

HRID 236107 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:28]2[CH2:32][CH2:31][NH:30][CH2:29]2)=[CH:23][CH:22]=1>O1CCCC1>[Cl:20][C:21]1[CH:22]=[CH:23][C:24]([S:27][CH:28]2[CH2:32][CH2:31][N:30]([C:1]([NH:8][CH2:12][CH2:11][N:10]([CH3:9])[CH3:13])=[O:2])[CH2:29]2)=[CH:25][CH:26]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 136079743-[(4-Chlorophenyl)sulfanyl]pyrrolidineHCID 57041336N,N-Dimethylaminoethylamine

Product 1

HCID 136080063-[(4-Chlorophenyl)thio]-N-[2-(dimethylamino)ethyl]-1-pyrrolidinecarboxamidYield 69.7%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 5.20 g (0.032 mole) of 1,1'-carbonyldiimidazole and 2.73 g (0.031 mole) of N,N-dimethylaminoethylamine in 200 ml of tetrahydrofuran was stirred at room temperature for 50 min. A solution of 5.63 g (0.0264 mole) of 3-[(4-chlorophenyl)thio]pyrrolidine (free base) in tetrahydrofuran was added and the solution was refluxed for about 66 hr. The solvent was removed in vacuo and the resulting oil was dissolved in methylene chloride. The methylene chloride solution was extracted with several portions of water and was dried over magnesium sulfate. The solvent was removed in vacuo and the resulting solid was recrystallized from methylene chloride-diethyl ether-hexane to give 6.03 g (69.7%) of white crystals, m.p. 97°-98.5° C.

Workup

  1. temperaturethe solution was refluxed for about 66 hr
  2. customThe solvent was removed in vacuo
  3. dissolutionthe resulting oil was dissolved in methylene chloride
  4. extractionThe methylene chloride solution was extracted with several portions of water
  5. dry with materialwas dried over magnesium sulfate
  6. customThe solvent was removed in vacuo
  7. customthe resulting solid was recrystallized from methylene chloride-diethyl ether-hexane

Sources & evidence

ORD record
ord-7ff3854e125145098828b0ff4464811a
Source dataset
uspto-grants-1987_02
Patent number
US04642348

Reaction notes

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