Water → HCID 12884420, compound

HRID 1701967Notes

Reaction equation

HRID 1701967 reaction equation
[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH2:21])(=[O:20])=[O:19])=[CH:14][CH:13]=1)=[O:8].[OH-].[Na+].O.[CH:25]1([N:31]=[C:32]=[O:33])[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]1>CC(C)=O>[O:1]=[C:2]1[CH2:6][CH2:5][CH2:4][N:3]1[C:7]([NH:9][CH2:10][CH2:11][C:12]1[CH:17]=[CH:16][C:15]([S:18]([NH:21][C:32]([NH:31][CH:25]2[CH2:30][CH2:29][CH2:28][CH2:27][CH2:26]2)=[O:33])(=[O:19])=[O:20])=[CH:14][CH:13]=1)=[O:8]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 18502Cyclohexyl isocyanateHCID 12884402HCID 12884402, compound

Product 1

HCID 12884420HCID 12884420, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g of 4-[2-(oxo-pyrrolidine-1-carboxamido)-ethyl]-benzenesulfonamide are dissolved in 100 ml of acetone with 0.65 g of NaOH and water. 2.3 g of cyclohexyl-isocyanate are added dropwise with agitation and ice cooling, and agitation is continued for 2 hours at room temperature. Subsequently, the substantial amount of acetone is distilled off under reduced pressure, the aqueous solution is acidified and the product is reprecipitated from dilute ammonia. The N-(4-[2-(2-oxo-pyrrolidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea is recrystallized from dilute ethanol, and has a melting point of 189°-190° C.

Workup

  1. distillationSubsequently, the substantial amount of acetone is distilled off under reduced pressure
  2. customthe product is reprecipitated from dilute ammonia
  3. customThe N-(4-[2-(2-oxo-pyrrolidine-1-carboxamido)-ethyl]-benzenesulfonyl)-N'-cyclohexyl urea is recrystallized from dilute ethanol

Sources & evidence

ORD record
ord-58a12e6a4e864aa1939913b1c25a9af7
Source dataset
uspto-grants-1983_04
Patent number
US04379785

Reaction notes

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