Butyl isocyanate → HCID 15225151, compound

HRID 274910Notes

Reaction equation

HRID 274910 reaction equation
C(N(CC)CC)C.[O:8]([C:15]1[CH:20]=[CH:19][C:18]([OH:21])=[CH:17][CH:16]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.[CH2:22]([N:26]=[C:27]=[O:28])[CH2:23][CH2:24][CH3:25]>C(Cl)Cl>[O:8]([C:15]1[CH:16]=[CH:17][C:18]([O:21][C:27](=[O:28])[NH:26][CH2:22][CH2:23][CH2:24][CH3:25])=[CH:19][CH:20]=1)[C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 132544-Phenoxyphenol

Product 1

HCID 15225151HCID 15225151, compoundYield 99.1%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Triethylamine (15 ml, 0.11 mol) was added dropwise under a nitrogen atmosphere to a solution of 4-phenoxyphenol (25.1 g, 0.14 mol) and butyl isocyanate (18 ml, 0.16 mol) in 400 ml of methylene chloride. After the addition, the solution was stirred overnight at room temperature. The solution was extracted with 1 N HCl, dried (MgSO4) and the solvent removed under reduced pressure to give 39.59 g of a tan solid. Recrystallization from diisopropyl ether gave the title compound as a white crystalline solid (21.01 g, 55%), mp 75°-77° C.

Workup

  1. additionAfter the addition
  2. extractionThe solution was extracted with 1 N HCl
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-3b2b6300caa6465698a337d16120f40d
Source dataset
uspto-grants-1995_02
Patent number
US05391571

Reaction notes

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