4-Chlorophenyl Isocyanate → HCID 86737164, compound

HRID 1856504Notes

Reaction equation

HRID 1856504 reaction equation
[N+:1]([CH2:4][C:5]([CH3:9])=[CH:6][CH2:7][OH:8])([O-:3])=[O:2].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=[O:19])=[CH:13][CH:12]=1>C1C=CC=CC=1>[CH3:9][C:5]([CH2:4][N+:1]([O-:3])=[O:2])=[CH:6][CH2:7][OH:8].[Cl:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18](=[O:2])[O-:19])=[CH:13][CH:12]=1

Participants

4

Reactant 2

HCID 76934-Chlorophenyl IsocyanateHCID 544391273-Methyl-4-nitrobut-2-en-1-ol

Product 1

HCID 86737164HCID 86737164, compound

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To 0.1 Mol of 4-nitro-3-methyl-2-butenol was added 0.1 Mol of melted p-chlorophenylisocyanate. The reaction mixture was allowed to stand at room temperature for several hours, before it was dissolved in hot benzene. After crystallizing overnight a solid by-product was filtered off and the benzene was evaporated. The residue was purified by dissolving in a hot hexane-benzene mixture, decanting, while hot, from an insoluble oil, followed by crystallization in a ice bath. The product was obtained as orange crystals, m.p. 79°-81°.

Workup

  1. waitto stand at room temperature for several hours, before it
  2. customAfter crystallizing overnight a solid by-product
  3. filtrationwas filtered off
  4. customthe benzene was evaporated
  5. customThe residue was purified
  6. dissolutionby dissolving in a hot hexane-benzene mixture
  7. customdecanting
  8. customwhile hot, from an insoluble oil, followed by crystallization in a ice bath
  9. customThe product was obtained as orange crystals, m.p. 79°-81°

Sources & evidence

ORD record
ord-e492f3e5e5cb477ead859b491bf855d2
Source dataset
uspto-grants-1980_08
Patent number
US04219660

Reaction notes

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