Dimethylformamide dimethyl acetal → HCID 178430874, compound

HRID 2297172Notes

Reaction equation

HRID 2297172 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])[CH2:10][C:11]1[NH:12][CH:13]=[C:14]([CH3:16])[N:15]=1.CO[CH:20](OC)[N:21]([CH3:23])[CH3:22]>>[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9](=[O:17])/[C:10](/[C:11]1[NH:12][CH:13]=[C:14]([CH3:16])[N:15]=1)=[CH:20]\[N:21]([CH3:23])[CH3:22]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 1784308761-(2,4-Dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one

Product 1

HCID 178430874HCID 178430874, compound

Conditions

Temperature
72.5 °C

Procedure

A mixture of 1-(2,4-dichlorophenyl)-2-(4-methylimidazol-2-yl)ethan-1-one (0.33 M) and N,N-dimethylformamide-dimethyl acetal (DMFDMA) (25 ml) was stirred for 2.5 h at 70-75° C. The DMFDMA was then removed under reduced pressure and dried under high vacuum for several hours giving a light orange solid in quantitative yield. The enaminone product (2Z)-1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methylimidazol-2-yl)prop-2-en-1-one was typically used without further purification.

Workup

  1. customThe DMFDMA was then removed under reduced pressure
  2. customdried under high vacuum for several hours
  3. customgiving a light orange solid in quantitative yield
  4. customThe enaminone product (2Z)-1-(2,4-dichlorophenyl)-3-(dimethylamino)-2-(4-methylimidazol-2-yl)prop-2-en-1-one was typically used without further purification

Sources & evidence

ORD record
ord-73c08f49afbb4d0eb279daed6d02d525
Source dataset
uspto-grants-2002_12
Patent number
US06489344B1

Reaction notes

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