Acetic Anhydride → HCID 66986224, compound

HRID 1254058Notes

Reaction equation

HRID 1254058 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[N:13]([CH3:14])[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[N:11][C:10]=2[C:21]2[CH:26]=[CH:25][C:24]([C:27]([OH:30])([CH3:29])[CH3:28])=[CH:23][CH:22]=2)=[CH:4][CH:3]=1.[C:31](OC(=O)C)(=[O:33])[CH3:32]>N1C=CC=CC=1.CN(C1C=CN=CC=1)C.CCOC(C)=O>[C:31]([O:30][C:27]([C:24]1[CH:23]=[CH:22][C:21]([C:10]2[N:11]=[C:12]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:13]([CH3:14])[C:9]=2[S:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:26][CH:25]=1)([CH3:28])[CH3:29])(=[O:33])[CH3:32]

Participants

6

Reactant 2

HCID 7918Acetic AnhydrideHCID 44553898HCID 44553898, compound

Product 1

HCID 66986224HCID 66986224, compound

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
60 °C

Procedure

To 2-(4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}phenyl)propan-2-ol (Example 73, 300 mg, 0.69 mmol) in 4 mL of pyridine and 4 mL of acetic anhydride was added catalytic amount of DMAP. After stirring at 60° C. for 2 hr, the reaction was diluted with EtOAc, washed with water and brine, dried over MgSO4, filtered, and concentrated to dryness to afford 1-(4-{5-[(4-chlorophenyl)thio]-1-methyl-2-phenyl-1H-imidazol-4-yl}phenyl)-1-methylethyl acetate which was used in the next step without further purification.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over MgSO4
  3. filtrationfiltered
  4. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-8da0b089527344b99aad825d082d6f9c
Source dataset
uspto-grants-2013_06
Patent number
US08455528B2

Reaction notes

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