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

HRID 1825438Notes

Reaction equation

HRID 1825438 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-fac3fc2db0744c5996157969c499850a
Source dataset
uspto-grants-2006_05
Patent number
US07045519B2

Reaction notes

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