Dimethylformamide dimethyl acetal → 4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile

HRID 31758Notes

Reaction equation

HRID 31758 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[C:2]1[CH2:6][C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:8].CO[CH:19](OC)[N:20]([CH3:22])[CH3:21]>>[CH3:19][N:20]([CH3:22])/[CH:21]=[C:6](\[C:2]1[NH:1][CH:5]=[CH:4][N:3]=1)/[C:7]([C:9]1[CH:14]=[CH:13][C:12]([C:15]#[N:16])=[CH:11][CH:10]=1)=[O:8]

Participants

3

Reactant 2

HCID 78373Dimethylformamide dimethyl acetalHCID 221429994-(2-Imidazolylacetyl)benzenecarbonitrile

Product 1

HCID 693105754-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile

Conditions

Temperature
75 °C

Procedure

A mixture of 4-(2-imidazolylacetyl)benzenecarbonitrile (0.30 M) and N,N-dimethylformamide dimethyl acetal (DMFDMA) (80 ml) was stirred for 12 h at 75° C. The DMFDMA was then removed under reduced pressure and dried under high vacuum for several hours giving an orange-yellow solid 4-[(2E)-3-(dimethylamino)-2-imidazolylprop-2-enoyl]benzenecarbonitrile in quantitative yield. The enaminone product was typically used without further purification.

Workup

  1. customThe DMFDMA was then removed under reduced pressure
  2. customdried under high vacuum for several hours

Sources & evidence

ORD record
ord-1d584f7ca362454b88ea8b457a67bd66
Source dataset
uspto-grants-2008_09
Patent number
US07425557B2

Reaction notes

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