Ethyl isocyanate → HCID 14855103, compound

HRID 1722393Notes

Reaction equation

HRID 1722393 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][S:10][C:11]2[NH:12][C:13]([CH3:30])=[C:14]([C:26]([O:28][CH3:29])=[O:27])[CH:15]([C:17]3[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=3)[N:16]=2)=[CH:5][CH:4]=1.[CH2:31]([N:33]=[C:34]=[O:35])[CH3:32].C(=O)([O-])[O-].[K+].[K+].ClCCl.CO>CC(C)=O>[CH2:31]([NH:33][C:34]([N:16]1[CH:15]([C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([N+:23]([O-:25])=[O:24])[CH:18]=2)[C:14]([C:26]([O:28][CH3:29])=[O:27])=[C:13]([CH3:30])[N:12]=[C:11]1[S:10][CH2:9][C:6]1[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=1)=[O:35])[CH3:32]

Participants

6

Reactant 4

HCID 8022Ethyl isocyanateHCID 11430Potassium CarbonateHCID 13885857HCID 13885857, compoundHCID 21226129Dichloromethane methanol

Product 1

HCID 14855103HCID 14855103, compoundYield 91.7%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A solution of 1,4-dihydro-2-[[(4-methoxyphenyl)methyl]thio]-6-methyl-4-(3-nitrophenyl)-5-pyrimidinecarboxylic acid, methyl ester (1.5 g, 3.5 mmole) in acetone under argon at room temperature was treated with ethyl isocyanate (0.5 ml, 0.45 g, 6.3 mmole) and powdered potassium carbonate (50 mg, 0.36 mmole). Examination of the reaction mixture using thin layer chromatography (tlc) (dichloromethane/methanol, 95:5) showed a new spot at higher Rf which did not increase after 1 to 2 hours. Volatiles were evaporated in vacuo and the residue was partitioned between ethyl acetate and water. The organic fraction was washed with water, 1N hydrochloric acid, water and saturated brine. The aqueous fractions were back-extracted with fresh ethyl acetate. The combined organic fractions were dried (magnesium sulfate) and concentrated in vacuo to give 1.6 g of crude product.

Workup

  1. temperaturedid not increase after 1 to 2 hours
  2. customVolatiles were evaporated in vacuo
  3. customthe residue was partitioned between ethyl acetate and water
  4. washThe organic fraction was washed with water, 1N hydrochloric acid, water and saturated brine
  5. extractionThe aqueous fractions were back-extracted with fresh ethyl acetate
  6. dry with materialThe combined organic fractions were dried (magnesium sulfate)
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-96a8aa8d39884ff482868eb798f53f61
Source dataset
uspto-grants-1989_08
Patent number
US04855301

Reaction notes

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