4-Bromoaniline → N-(4-bromophenyl)-5-methoxy-1,3-benzothiazol-2-amine

HRID 2070244Notes

Reaction equation

HRID 2070244 reaction equation
Br[C:2]1[S: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>CN1C(=O)CCC1>[Br:13][C:14]1[CH:20]=[CH:19][C:17]([NH:18][C:2]2[S: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 220405252-Bromo-5-methoxybenzothiazole

Product 1

HCID 7489958N-(4-bromophenyl)-5-methoxy-1,3-benzothiazol-2-amine

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

The mixture containing 2-bromo-5-methoxybenzthiazole (1 eq), 4-Bromoaniline (2 eq) and diisopropylethylamine was subjected to microwave in NMP at 220° C. 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 the desired product. MS: MH+=335

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-5a826e85747f49ed9ed5376897a3df2f
Source dataset
uspto-grants-2012_10
Patent number
US08299108B2

Reaction notes

Loading…