4-Bromoaniline → (4-Bromophenyl)(5-methoxybenzoxazol-2-yl)amine

HRID 1915632Notes

Reaction equation

HRID 1915632 reaction equation
Cl[C:2]1[O:3][C:4]2[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:5]=2[N:6]=1.[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH2:18])=[CH:16][CH:15]=1.C(N(C(C)C)CC)(C)C>CN(C)C=O>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[O:3][C:4]3[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][C:5]=3[N:6]=2)=[CH:16][CH:15]=1

Participants

5

Reactant 3

HCID 78074-BromoanilineHCID 81531DiisopropylethylamineHCID 118197122-Chloro-5-methoxy-1,3-benzoxazole

Product 1

HCID 22040817(4-Bromophenyl)(5-methoxybenzoxazol-2-yl)amine

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The mixture containing 2-chloro-5-methoxybenzoxazole (1 eq), 4-bromoaniline (2 eq) and diisopropylethylamine was refluxed in dimethylformamide. The resultant mixture was concentrated and partitioned between ethyl acetate and water. The organic layer was washed with brine and dried. Purification on silica gel gave (4-bromophenyl)(5-methoxybenzoxazol-2-yl)amine. MS: MH+=318

Workup

  1. concentrationThe resultant mixture was concentrated
  2. custompartitioned between ethyl acetate and water
  3. washThe organic layer was washed with brine
  4. customdried
  5. customPurification on silica gel

Sources & evidence

ORD record
ord-3e1a9ac56d5741b4a5f610f9f8fbfbe6
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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