Phenyl isocyanate → HCID 131717237, compound

HRID 2373086Notes

Reaction equation

HRID 2373086 reaction equation
[CH:1]([Si:4]([CH:23]([CH3:25])[CH3:24])([CH:20]([CH3:22])[CH3:21])[C:5]1([CH2:18][OH:19])[C:17]2[CH:16]=[CH:15][CH:14]=[CH:13][C:12]=2[C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2)([CH3:3])[CH3:2].[C:26]1([N:32]=[C:33]=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>C1C=CC=CC=1.C(N(CC)CC)C>[C:33](=[O:34])([O:19][CH2:18][C:5]1([Si:4]([CH:1]([CH3:3])[CH3:2])([CH:20]([CH3:22])[CH3:21])[CH:23]([CH3:25])[CH3:24])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:11]=2[C:12]2[C:17]1=[CH:16][CH:15]=[CH:14][CH:13]=2)[NH:32][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 19902683HCID 19902683, compound

Product 1

HCID 131717237HCID 131717237, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Conditions

Temperature
82 °C

Procedure

To a mixture of 1.0 g of 9-triisopropylsilyl-9-fluorenemethanol and 0.3 mL of phenyl isocyanate in 10 mL of dry benzene was added 2 drops of triethylamine. The mixture was heated in an oil bath at 82° C. for one hour and cooled to room temperature. The solvent was evaporated in vacuo to give 1.30 g (100%) of the crude urethane as a yellow solid. Recrystallization from Skelly B gave 1.12 g (86.02%) of the pure urethane as colorless crystals, m.p. 152.5°-154° C.; IR (KBr): 3240 (NH), 1690 (C=O) cm-1 ; 1H NMR (CDCl3); δ 0.87 (d, 18H, Si-C-Me2), 1.18-1.44 (hept, 3H, C-Si-CH), 5.33 (s, 2H, CH2), 6.02 (b, 1H, NH), 6.70-7.95 (m, 13H, aryl).

Workup

  1. temperaturecooled to room temperature
  2. customThe solvent was evaporated in vacuo

Sources & evidence

ORD record
ord-4a8814970988427e8c8d11938c45fcd2
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

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