2-Amino-4-methylphenol → N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amine

HRID 897917Notes

Reaction equation

HRID 897917 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([CH3:8])[CH:5]=[CH:4][C:3]=1[OH:9].[Br:10][C:11]1[CH:16]=[CH:15][C:14]([N:17]=[C:18]=S)=[CH:13][CH:12]=1.C(N(CC)CC)C>O1CCCC1.S([O-])([O-])(=O)=O.[Cu+2]>[Br:10][C:11]1[CH:16]=[CH:15][C:14]([NH:17][C:18]2[O:9][C:3]3[CH:4]=[CH:5][C:6]([CH3:8])=[CH:7][C:2]=3[N:1]=2)=[CH:13][CH:12]=1

Participants

6

Reactant 3

HCID 72642-Amino-4-methylphenolHCID 8471TriethylamineHCID 161334-Bromophenyl isothiocyanate

Product 1

HCID 21985825N-(4-Bromophenyl)-5-methyl-1,3-benzoxazol-2-amineYield 81.2%

Reagents, catalysts & solvents 2

HCID 24462Copper SulfateCatalystHCID 8028TetrahydrofuranSolvent

Procedure

2-Amino-4-methylphenol (1.15 g, 9.34 mmol) was added to a solution of 4-bromophenyl isothiocyanate (2.00 g, 9.34 mmol) in tetrahydrofuran (35 mL) and the reaction was stirred at room temperature for 16 h. Anhydrous copper (II) sulfate (14.06 g, 88.10 mmol), silica gel (14.06 g), and triethylamine (1.3 mL, 9.34 mmol) were added, and the mixture was stirred at room temperature for 24 h. The reaction was concentrated under reduced pressure and then added to a silica pad and purified using 1:5 ethyl acetate:heptane (2 L) followed by diethyl ether as the eluent to afford N2-(4-bromophenyl)-5-methyl-1,3-benzoxazol-2-amine as a light brown solid (2.30 g, 81%);

Workup

  1. stirringthe mixture was stirred at room temperature for 24 h
  2. concentrationThe reaction was concentrated under reduced pressure
  3. additionadded to a silica pad
  4. custompurified

Sources & evidence

ORD record
ord-01aea736a1b54e418366820b21c6b3aa
Source dataset
uspto-grants-2005_07
Patent number
US06921763B2

Reaction notes

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