Dimethylformamide → HCID 18404772, compound

HRID 1003423Notes

Reaction equation

HRID 1003423 reaction equation
[CH:1]1([CH2:4][O:5][CH2:6][C:7]([C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)[CH2:3][CH2:2]1.C[N:16](C)[CH:17]=[O:18].COC(OC)N(C)C.[C:28]([CH2:30][C:31](N)=O)#[N:29]>C(OCC)C.O>[C:28]([C:30]1[C:17](=[O:18])[NH:16][C:11]([C:12]2[CH:13]=[CH:14][CH:9]=[CH:7][C:6]=2[O:5][CH2:4][CH:1]2[CH2:2][CH2:3]2)=[CH:10][CH:31]=1)#[N:29]

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 7898CyanoacetamideHCID 78373Dimethylformamide dimethyl acetalHCID 11183110HCID 11183110, compound

Product 1

HCID 18404772HCID 18404772, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3283Diethyl EtherSolvent

Conditions

Temperature
140 °C

Procedure

A stirred mixture of 2-(cyclopropylmethoxy)-acetophenone (15 g), dimethylformamide (45 ml) and dimethylformamide dimethylacetal (12.75 ml) was heated at 140° C. for 25 hours, then cyanoacetamide (8.29 g) was added and the mixture was heated for a further 18 hours. The cool mixture was added to water (200 ml) and diethyl ether (100 ml) and the solid was collected by filtration, washed with water then with ethanol. Digestion with acetonitrile give the title compound, 6.1 g, m.p. 250°-252° C. (from acetonitrile).

Workup

  1. temperaturethe mixture was heated for a further 18 hours
  2. filtrationthe solid was collected by filtration
  3. washwashed with water

Sources & evidence

ORD record
ord-e0fea494fc104e958115cbcf5092084c
Source dataset
uspto-grants-2000_04
Patent number
US06046216

Reaction notes

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