Methyl Isocyanate → 1-{1,2-Dimethyl-1-[(p-tolylsulfonyl)carbamoyl]propyl}-3-methylurea

HRID 275047Notes

Reaction equation

HRID 275047 reaction equation
Cl.[NH2:2][C:3]([CH3:20])([CH:17]([CH3:19])[CH3:18])[C:4]([NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])=[O:5].[CH3:21][N:22]=[C:23]=[O:24]>CN(C=O)C.C1COCC1>[CH3:20][C:3]([NH:2][C:23]([NH:22][CH3:21])=[O:24])([C:4](=[O:5])[NH:6][S:7]([C:10]1[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=1)(=[O:9])=[O:8])[CH:17]([CH3:18])[CH3:19]

Participants

5

Reactant 2

HCID 12228Methyl IsocyanateHCID 200898702-Amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride

Product 1

HCID 146957621-{1,2-Dimethyl-1-[(p-tolylsulfonyl)carbamoyl]propyl}-3-methylurea

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-30 °C

Procedure

A solution of 2-amino-2,3-dimethyl-N-(p-tolylsulfonyl)butyramide hydrochloride (5 g, 15.58 mmols) dissolved in 50 mL of DMF under nitrogen is cooled to -30° C. Then 10 mL of methyl isocyanate in 10 mL of THF is added at such a rate that temperature is maintained at -30° C., and the reaction mixture is allowed to stir for two hours at -30° C. and then for 16 hours at room temperature.

Workup

  1. temperatureis maintained at -30° C.
  2. waitfor 16 hours at room temperature

Sources & evidence

ORD record
ord-fc52b1b52e1f4443a292027f5bdf946b
Source dataset
uspto-grants-1995_02
Patent number
US05391757

Reaction notes

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