Chlorophenyl isocyanate → HCID 19973936, compound

HRID 1451156Notes

Reaction equation

HRID 1451156 reaction equation
[NH2:1][C:2]([C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4].[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[N:28]=[C:29]=[O:30]>C(OCC)(=O)C>[Cl:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=1[NH:28][C:29](=[O:30])[NH:1][C:2]([C:11]1[N:16]=[C:15]([O:17][CH3:18])[CH:14]=[C:13]([O:19][CH3:20])[N:12]=1)([CH:8]([CH3:10])[CH3:9])[C:3]([O:5][CH2:6][CH3:7])=[O:4]

Participants

4

Reactant 2

HCID 76833Chlorophenyl isocyanateHCID 19973933HCID 19973933, compound

Product 1

HCID 19973936HCID 19973936, compoundYield 88.6%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

A solution of ethyl 2-amino-3-methyl-2-(4,6-dimethoxypyrimidin-2-yl)butanoate (0.556 g) and 2-chlorophenylisocyanate (0.306 g) in ethyl acetate (30 ml) was refluxed for 5 hours, evaporated to dryness, and flash chromatographed on silica gel, eluting with ethyl acetate/60°-80° petroleum ether (1:2). The residual gum was triturated with 60°-80° petroleum ether, to give 0.76 g of the desired product as a white solid, mp 84°-87° C.

Workup

  1. customevaporated to dryness, and flash
  2. customchromatographed on silica gel
  3. washeluting with ethyl acetate/60°-80° petroleum ether (1:2)
  4. customThe residual gum was triturated with 60°-80° petroleum ether

Sources & evidence

ORD record
ord-f73cd06ff3be433ca9b62d9b0dedba5f
Source dataset
uspto-grants-1997_02
Patent number
US05604181

Reaction notes

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