Butyl isocyanate → Butylcarbamic acid 2-dibenzofuranyl ester

HRID 1609575Notes

Reaction equation

HRID 1609575 reaction equation
[OH:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][C:8]=3[C:4]=2[CH:3]=1.[CH2:15]([N:19]=[C:20]=[O:21])[CH2:16][CH2:17][CH3:18].C(N(CC)CC)C>C(Cl)Cl>[CH:3]1[C:4]2[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=3[O:6][C:5]=2[CH:13]=[CH:14][C:2]=1[O:1][C:20](=[O:21])[NH:19][CH2:15][CH2:16][CH2:17][CH3:18]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 8471TriethylamineHCID 665872-Dibenzofuranol

Product 1

HCID 15229765Butylcarbamic acid 2-dibenzofuranyl esterYield 54.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 2-hydroxydibenzofuran (1.47 g, 7.98 mmol), butyl isocyanate (1.26 mL, 11.2 mmol) and triethylamine (0.89 mL, 6.39 mmol) in 50 mL of methylene chloride was stirred under N2 at room temperature for 1 hour. The solvent was removed under reduced pressure to give a solid. Recrystallization from diethyl etherhexane gave 1.23 g (54%) of the title compound as a white crystalline solid, mp 124°-126° C.

Workup

  1. customThe solvent was removed under reduced pressure
  2. customto give a solid
  3. customRecrystallization from diethyl etherhexane

Sources & evidence

ORD record
ord-320ddf506f7745449d8ee28d95b64d7f
Source dataset
uspto-grants-1995_03
Patent number
US05401769

Reaction notes

Loading…