tert-Butyl isocyanate → N-t-Butyl-N'-(2-hydroxy-4-nitrophenyl)urea

HRID 368379Notes

Reaction equation

HRID 368379 reaction equation
[C:1]([N:5]=[C:6]=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18]>C1(C)C=CC=CC=1>[C:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][C:10]=1[OH:18])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 62412tert-Butyl isocyanateHCID 49847212-Amino-5-Nitrophenol

Product 1

HCID 23288442N-t-Butyl-N'-(2-hydroxy-4-nitrophenyl)urea

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of t-butyl isocyanate (400 mg, 4.04 mmol) in toluene, the 2-amino-5-nitrophenol (622 mg, 4.04 mmol) was added. The reaction mixture was stirred at 80° C. for 24 hours, then cooled to room temperature. The product was purified by precipitation from toluene and filtering (864 mg, 85%). m.p: 99.0-101.1° C.; EI-MS m/z 254 (M+H)+.

Workup

  1. temperaturecooled to room temperature
  2. customThe product was purified by precipitation from toluene
  3. filtrationfiltering (864 mg, 85%)

Sources & evidence

ORD record
ord-b01844586da94ec988f3e4ffdba39488
Source dataset
uspto-grants-2000_10
Patent number
US06133319

Reaction notes

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