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

HRID 1790667Notes

Reaction equation

HRID 1790667 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-bromo-phenyl)(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-d46419144c4b457395c31c7c0a85f395
Source dataset
uspto-grants-2006_07
Patent number
US07071216B2

Reaction notes

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