Phenyl isocyanate → 9-Xanthenylmethyl Carbanilate

HRID 2373077Notes

Reaction equation

HRID 2373077 reaction equation
[CH:1]1[C:14]2[CH:13]([CH2:15][OH:16])[C:12]3[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=3)[O:6][C:5]=2[CH:4]=[CH:3][CH:2]=1.[C:17]1([N:23]=[C:24]=[O:25])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1C=CC=CC=1.C(N(CC)CC)C>[C:24](=[O:25])([O:16][CH2:15][CH:13]1[C:12]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:6][C:5]2[C:14]1=[CH:1][CH:2]=[CH:3][CH:4]=2)[NH:23][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 7672Phenyl isocyanateHCID 28015919H-Xanthene-9-methanol

Product 1

HCID 538340119-Xanthenylmethyl CarbanilateYield 95.2%

Reagents, catalysts & solvents 2

HCID 8471TriethylamineCatalystHCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

To a mixture of 1.0 g of 9-xanthenemethanol and 0.51 mL of phenyl isocyanate in 5.0 mL of dry benzene was added two drops of triethylamine. The mixture was heated in an oil bath at 80° C. for 20 hours and cooled in an ice bath for 2 hours. The precipitated crystals were filtered and rinsed with Skelly B to give 1.48 g (95.2%) of the crude urethane as white crystals. Recrystallization from EtOAc--Skelly B (5:1) gave 1.37 g (88.1%) of the pure Xmoc-aniline as white needles, m.p. 180°-181° C.; IR (KBr): 3350 (NH), 1705 (C=O) cm-1 ; 1H NMR (CDCl3): δ 4.30 (m, 3H, CHCH2O), 6.55 (b, 1H, NH , 6.90-7.40 (m, 13H, aryl).

Workup

  1. temperaturecooled in an ice bath for 2 hours
  2. filtrationThe precipitated crystals were filtered
  3. washrinsed with Skelly B

Sources & evidence

ORD record
ord-73a420c0daf34fe5a2981dbf3aff983d
Source dataset
uspto-grants-1992_03
Patent number
US05101059

Reaction notes

Loading…