Phenyl isocyanate → HCID 54423781, compound

HRID 2373082Notes

Reaction equation

HRID 2373082 reaction equation
[CH3:1][Si:2]([CH3:19])([CH3:18])[C:3]1([CH2:16][OH:17])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2.[C:20]1([N:26]=[C:27]=[O:28])[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>C1C=CC=CC=1>[C:27](=[O:28])([O:17][CH2:16][C:3]1([Si:2]([CH3:19])([CH3:18])[CH3:1])[C:15]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[C:9]2[C:4]1=[CH:5][CH:6]=[CH:7][CH:8]=2)[NH:26][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1

Participants

4

Reactant 2

HCID 7672Phenyl isocyanateHCID 19902664HCID 19902664, compound

Product 1

HCID 54423781HCID 54423781, compoundYield 91.9%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 1.0 g of 9-trimethylsilyl-9-fluorenemethanol and 0.4 mL of phenyl isocyanate in 2.0 mL of dry benzene was heated in an oil bath at 80° C. for seven hours. The mixture was cooled to room temperature and triturated with 20 mL of Skelly F. The crystals deposited were removed by filtration, rinsed with Skelly F, and recrystallized from Skelly B to give 1.31 g (91.9%) of the urethane as white crystals, m.p. 137°-138° C.; IR(KBr): 3300 (NH), 1700 (C=O) cm-1 ; 1H NMR (CDCl3) 5 -0.12 (s, 9H, SiMe3), 5.07 (s, 2H, CH2), 6.21 (b, 1H, NH), 6.80-8.00 (m, 13H, aryl).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. customtriturated with 20 mL of Skelly F
  3. customThe crystals deposited were removed by filtration
  4. washrinsed with Skelly F
  5. customrecrystallized from Skelly B

Sources & evidence

ORD record
ord-08e1793910f44a6da6e798192f787977
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

Loading…