Methyl Isocyanate → HCID 18626626, compound

HRID 1860151Notes

Reaction equation

HRID 1860151 reaction equation
[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=2)[C:8]([NH2:10])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1.[CH3:24][N:25]=[C:26]=[O:27]>C1(C)C=CC=CC=1>[CH:1]1([CH2:6][CH:7]([C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[C:13]([N+:21]([O-:23])=[O:22])[CH:12]=2)[C:8]([NH:10][C:26]([NH:25][CH3:24])=[O:27])=[O:9])[CH2:5][CH2:4][CH2:3][CH2:2]1

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18626641HCID 18626641, compound

Product 1

HCID 18626626HCID 18626626, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
120 °C

Procedure

A solution of 3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionamide (126 mg, 0.37 mmol) and methyl isocyanate (211 mg, 3.70 mmol) in toluene (2 mL) was heated under reflux (120° C.) for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo. The resulting yellow oil was treated with a small amount of a 1/1 mixture of hexanes/ethyl acetate, and a precipitate started to form. The material was further cooled in the freezer for 2 h to facilitate additional precipitation. The solid was collected by filtration and then dried in vacuo to afford 1-[3-cyclopentyl-2-(4-methanesulfonyl-3-nitrophenyl)-propionyl]-3-methyl-urea (50 mg, 35%) as a pale yellow solid: mp 241-242° C.; FAB-HRMS m/e calcd for C17H23N3O6S (M+H)+398.1386, found 398.1399.

Workup

  1. temperatureto cool to 25° C.
  2. concentrationconcentrated in vacuo
  3. additionThe resulting yellow oil was treated with a small amount of a 1/1 mixture of hexanes/ethyl acetate
  4. customto form
  5. temperatureThe material was further cooled in the freezer for 2 h
  6. customprecipitation
  7. filtrationThe solid was collected by filtration
  8. customdried in vacuo

Sources & evidence

ORD record
ord-43324a017e994a5c9334b77f774caa65
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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