Methyl vinyl sulfone → HCID 59485596, compound

HRID 1972262Notes

Reaction equation

HRID 1972262 reaction equation
[Cl:1][C:2]1[CH:34]=[CH:33][C:5]([O:6][C:7]2[CH:12]=[CH:11][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:19]=4)[CH2:16][NH:15][C:14]3=[O:32])=[CH:9][CH:8]=2)=[CH:4][CH:3]=1.[H-].[Na+].[CH:37]([S:39]([CH3:42])(=[O:41])=[O:40])=[CH2:38].[Cl-].[NH4+]>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([N:13]3[CH:17]([C:18]4[CH:23]=[CH:22][CH:21]=[C:20]([O:24][CH2:25][C:26]5[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=5)[CH:19]=4)[CH2:16][N:15]([CH2:38][CH2:37][S:39]([CH3:42])(=[O:41])=[O:40])[C:14]3=[O:32])=[CH:11][CH:12]=2)=[CH:33][CH:34]=1

Participants

6

Reactant 4

HCID 19354Methyl vinyl sulfoneHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 59485675HCID 59485675, compound

Product 1

HCID 59485596HCID 59485596, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To 1-(4-(4-chlorophenoxy)phenyl)-5-(3-(benzyloxy)phenyl)imidazolidin-2-one (Example 288) (200 mg, 0.42 mmol) in 5 mL DMF is added sodium hydride (19 mg, 0.47 mmol) followed by methyl vinyl sulfone (41 μL, 0.47 mmol). After 30 minute, the reaction is cooled to 0° C. and sat. ammonium chloride is added slowly to the reaction mixture. The reaction mixture is extracted with ethyl acetate (2×) and purified by flash chromatography gives 171 mg (71%) of the title compound. HPLC-MS calculated for C31H29ClN2O5S (M+H+): 577.2, found 577.2.

Workup

  1. extractionThe reaction mixture is extracted with ethyl acetate (2×)
  2. custompurified by flash chromatography

Sources & evidence

ORD record
ord-bbf50190400e4351a39e624b9c46173c
Source dataset
uspto-grants-2013_04
Patent number
US08431607B2

Reaction notes

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