tert-Butanol → t-Butyl carbanilate

HRID 1440222Notes

Reaction equation

HRID 1440222 reaction equation
[C:1]1([N:7]=[C:8]=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:10]([OH:14])([CH3:13])([CH3:12])[CH3:11]>C1(C)C=CC=CC=1>[C:8]([NH:7][C:1]1[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1)([O:14][C:10]([CH3:13])([CH3:12])[CH3:11])=[O:9]

Participants

4

Reactant 2

HCID 6386tert-ButanolHCID 7672Phenyl isocyanate

Product 1

HCID 137930t-Butyl carbanilate

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
50 °C

Procedure

Phenylisocyanate (500 g) and tert-butanol (500 mL) are mixed in toluene (500 mL) in a 2 L round bottom flask. The solution is stirred over night in a 50° C. water bath. The N-Boc aniline is collected by filtration to give the white solid (702 g).

Workup

  1. filtrationThe N-Boc aniline is collected by filtration

Sources & evidence

ORD record
ord-32f4aef637c246e3b91b86b5e11b4d9b
Source dataset
uspto-grants-1996_03
Patent number
US05498624

Reaction notes

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