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

HRID 1915619Notes

Reaction equation

HRID 1915619 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>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

4

Reactant 2

HCID 78074-BromoanilineHCID 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 disopropylethylamine 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-4666367294094b81a2421eaec8592c3a
Source dataset
uspto-grants-2013_12
Patent number
US08614330B2

Reaction notes

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