2,6-Dimethylaniline → HCID 70546412, compound

HRID 2286453Notes

Reaction equation

HRID 2286453 reaction equation
[C:1]([C:3](=[CH:12]OCC)[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2].[CH3:16][C:17]1[CH:23]=[CH:22][CH:21]=[C:20]([CH3:24])[C:18]=1[NH2:19].CCCCCC>C(O)C>[C:1]([C:3](=[CH:12][NH:19][C:18]1[C:20]([CH3:24])=[CH:21][CH:22]=[CH:23][C:17]=1[CH3:16])[C:4]([NH:6][C:7]([O:9][CH2:10][CH3:11])=[O:8])=[O:5])#[N:2]

Participants

5

Reactant 3

HCID 68962,6-Dimethylaniline2×HCID 8058HexaneHCID 230015ethyl N-(2-cyano-3-ethoxyacryloyl)carbamate

Product 1

HCID 70546412HCID 70546412, compoundYield 73.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of α-cyano-β-ethoxy-N-ethoxycarbonylacrylamide (0.05 mol) and 2,6-dimethylaniline (0.05 mol) in 75 ml ethanol is refluxed for several hours until the 2,6-dimethylaniline disappears as checked by thin layer chromatography. On cooling, (precipitate not formed) hexane (about 400 ml) is added and the mixture is filtered to yield 10.52 g of α-cyano-β-(2,6-dimethylanilino)-N-ethoxycarbonylacrylamide, m.p. 138°-140°, which is cyclized by heating in ortho-dichlorobenzene for about 4 hours to yield 5-cyano-1-(2,6-dimethylphenyl)uracil.

Workup

  1. temperatureOn cooling
  2. additionis added
  3. filtrationthe mixture is filtered

Sources & evidence

ORD record
ord-ca3d5ef3365b4857bacb53c5c760362d
Source dataset
uspto-grants-1981_05
Patent number
US04266056

Reaction notes

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