Methyl Isocyanate → HCID 12044472, compound

HRID 1860204Notes

Reaction equation

HRID 1860204 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]([CH:13]([CH2:17][CH:18]2[CH2:22][CH2:21][CH2:20][CH2:19]2)[C:14]([NH2:16])=[O:15])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:11])=[O:10])#[N:2].[CH3:23][N:24]=[C:25]=[O:26]>C1(C)C=CC=CC=1>[C:1]([C:3]1[CH:4]=[C:5]([CH:13]([CH2:17][CH:18]2[CH2:19][CH2:20][CH2:21][CH2:22]2)[C:14]([NH:16][C:25]([NH:24][CH3:23])=[O:26])=[O:15])[CH:6]=[CH:7][C:8]=1[S:9]([CH3:12])(=[O:10])=[O:11])#[N:2]

Participants

4

Reactant 2

HCID 12228Methyl IsocyanateHCID 18626624HCID 18626624, compound

Product 1

HCID 12044472HCID 12044472, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionamide (135 mg, 0.42 mmol) and methyl isocyanate (72 mg, 1.26 mmol) in toluene (1 mL) was heated under reflux for 15 h. The reaction mixture was allowed to cool to 25° C. and then concentrated in vacuo to afford a yellow semi-solid. The semi-solid was treated with a solution of 2/1 hexanes/ethyl acetate (3 mL) and a white precipitate formed. The suspension was placed in the freezer for 1 h and then filtered to afford 1-[2-(3-cyano-4-methanesulfonyl-phenyl)-3-cyclopentyl-propionyl]-3-methyl-urea (55 mg, 35%) as a white solid: mp 237-239° C.; FAB-HRMS m/e calcd for C18H23N3O4S (M+H)+378.1487, found 378.1483.

Workup

  1. temperatureunder reflux for 15 h
  2. concentrationconcentrated in vacuo
  3. customto afford a yellow semi-solid
  4. customa white precipitate formed
  5. filtrationfiltered

Sources & evidence

ORD record
ord-061b4d3fdaa24c17b3f847b44846f71a
Source dataset
uspto-grants-2003_03
Patent number
US06528543B1

Reaction notes

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