Dimethylacetamide → HCID 57807799, compound

HRID 2105126Notes

Reaction equation

HRID 2105126 reaction equation
[NH:1]([C:8]1[N:13]=[C:12]([C:14]2N3CCCC3=NC=2)[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:22](=[O:25])(O)O.C1(NC(N)=N)C=CC=CC=1.C[C:37](N(C)C)=[O:38]>>[NH:1]([C:8]1[N:13]=[C:12]([CH:14]([O:25][CH3:22])[O:38][CH3:37])[CH:11]=[CH:10][N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 31374DimethylacetamideHCID 11311952HCID 11311952, compoundHCID 16217093Carbonic acid, compound with phenylguanidine (1:1)

Product 1

HCID 57807799HCID 57807799, compoundYield 88%

Conditions

Temperature
130 °C

Procedure

A mixture of 1,1-dimethoxy-4-dimethylaminobut-3-en-2-one (Method 1; 20.0 g, 0.116 mol) and phenyl guanidine bicarbonate (25 g, 0.126 mol) in anhydrous dimethylacetamide (350 ml) was stirred and heated at 130° C. under nitrogen for 18 hours. The reaction mixture was allowed to cool and the solvent removed by evaporation. The residue was dissolved in EtOAc and the solution washed with water (×5), saturated sodium chloride (×2), dried and evaporated to give the title compound (24.7 g, 88%) as a dark brown oil. NMR: (CDCl3): 3.42 (s, 6H), 5.20 (s, 1H), 6.94 (d, 1H), 7.04 (t, 1H), 7.31 (m, 3H), 7.64 (d, 2H), 8.47 (d, 1H), m/z: 246.

Workup

  1. temperatureto cool
  2. customthe solvent removed by evaporation
  3. dissolutionThe residue was dissolved in EtOAc
  4. washthe solution washed with water (×5), saturated sodium chloride (×2)
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-c773cfd7f8db4937b92ad816c6476972
Source dataset
uspto-grants-2009_08
Patent number
US07579344B2

Reaction notes

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