Dimethylformamide dimethyl acetal → 1-(N,N-dimethylamino)-3-(4-fluorophenyl)-2-[4-(methylthio)phenyl]prop-1-en-3-one

HRID 1416959Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8](=[O:18])[CH2:9][C:10]2[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=2)=[CH:4][CH:3]=1.CO[CH:21](OC)[N:22]([CH3:24])[CH3:23]>CN(C)C=O>[CH3:21][N:22]([CH:24]=[C:9]([C:10]1[CH:15]=[CH:14][C:13]([S:16][CH3:17])=[CH:12][CH:11]=1)[C:8]([C:5]1[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=1)=[O:18])[CH3:23]

Participants

Conditions

Temperature: 75 °C

Procedure

To a 500 ml 2-necked flask fitted with a thermometer and magnetic stirrer was added 20 g (76.9 mMol) of 1-(4-fluorophenyl)-2-(4-(methylthio)phenyl)ethan-1-one, Example 1, Step 3, 18.3 g (154 mMol) of dimethylformamide dimethyl acetal and 50 ml dry dimethylformamide (DMF). The reaction mixture was heated to 75° C. for 3 hours, cooled to room temperature and evaporated to dryness and to recover 26.1 g a yellowish orange solid.

Workup

customTo a 500 ml 2-necked flask fitted with a thermometer and magnetic stirrer
temperaturecooled to room temperature
customevaporated to dryness
customto recover 26.1 g a yellowish orange solid

Sources & evidence

ORD record: ord-26fabde7c9e6485097e948347856e19d
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05916905

Reaction notes

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