Phenyl isocyanate → HCID 19804385, compound

HRID 1681919Notes

Reaction equation

HRID 1681919 reaction equation
[N+:1]([CH2:4][CH2:5][CH3:6])([O-:3])=O.[Cl:7]CCCC#C.[C:13]1(N=C=O)[CH:18]=[CH:17]C=CC=1.C(N([CH2:27][CH3:28])CC)C>C1(C)C=CC=CC=1>[Cl:7][CH:18]([CH3:17])[CH2:13][C:6]1[O:3][N:1]=[C:4]([CH2:27][CH3:28])[CH:5]=1

Participants

6

Reactant 4

HCID 7672Phenyl isocyanateHCID 79031-NitropropaneHCID 8471TriethylamineHCID 843081-Pentyne, 5-chloro-

Product 1

HCID 19804385HCID 19804385, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A mixture of 11.56 g 1-nitropropane, 15 g 1-chloro-4-pentyne [HC≡C(CH2)3Cl], 37 g phenylisocyanate and 4 ml triethylamine in 300 ml toluene was stirred at room temperature for three days. The reaction mixture was filtered, the filtrate concentrated in vacuo, and the residue chromatographed (silica gel, eluted with hexane and 20% ethyl acetate in hexane) to give 12 g 5-(2-chloropropyl)-3-ethylisoxazole as a yellow oil.

Workup

  1. filtrationThe reaction mixture was filtered
  2. concentrationthe filtrate concentrated in vacuo
  3. customthe residue chromatographed
  4. wash(silica gel, eluted with hexane and 20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-4b0f623d178a496390b1aa9e1bcf280f
Source dataset
uspto-grants-1992_12
Patent number
US05175178

Reaction notes

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