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Methyl Isocyanate → 1-[2-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea

HRID 1860197
Notes
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Reaction equation

HRID 1860197 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH2:15])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9].[CH3:22][N:23]=[C:24]=[O:25]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([CH:12]([CH2:16][CH:17]2[CH2:21][CH2:20][CH2:19][CH2:18]2)[C:13]([NH:15][C:24]([NH:23][CH3:22])=[O:25])=[O:14])[CH:5]=[CH:6][C:7]=1[S:8]([CH3:11])(=[O:10])=[O:9]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 186266382-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide

Product 1

HCID 186266221-[2-(3-Bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-ureaYield 44%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (200 mg, 0.53 mmol) and methyl isocyanate (61 mg, 1.07 mmol) in toluene (1 mL) was heated under reflux for 24 h. The reaction mixture turned very cloudy with the forming of a white precipitate. The reaction mixture was allowed to cool to 25° C. and then treated with hexanes. The reaction mixture was placed in the freezer for 1 h then filtered. The white solid was washed with cold hexanes to afford 1-[2-(3-bromo-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (100 mg, 44%) as a white solid: mp 259-260° C.; FAB-HRMS m/e calcd for C17H23BrN2O4S (M+H)+431.0641, found 431.0646.

Workup

  1. temperatureunder reflux for 24 h
  2. customforming of a white precipitate
  3. filtrationthen filtered
  4. washThe white solid was washed with cold hexanes

Sources & evidence

ORD record
ord-d543536659414bd1b5ebfa0a037ad390
Source dataset
uspto-grants-2003_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06528543B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes