4-Aminophenol → HCID 18932285, compound

HRID 1597773Notes

Reaction equation

HRID 1597773 reaction equation
Br[CH2:2][C:3]1[S:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH2:18][C:19]1[CH:24]=[CH:23][C:22]([OH:25])=[CH:21][CH:20]=1>CC(C)=O>[S:4]1[C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=[C:3]1[CH2:2][O:25][C:22]1[CH:23]=[CH:24][C:19]([NH2:18])=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 4034-AminophenolHCID 10796Cesium carbonate2×HCID 27762582-(Bromomethyl)-1,3-benzothiazole

Product 1

HCID 18932285HCID 18932285, compoundYield 52.4%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

4.56 g of 2-bromomethylbenzothiazole and 3.25 g of cesium carbonate were added to a solution of 2.17 g of 4-aminophenol in 70 ml of acetone, and the resulting mixture was stirred at room temperature for 8.5 hours, after which a further 3.25 g of cesium carbonate were added and the reaction mixture was stirred at room temperature for a further 4 hours. The reaction mixture was then filtered and the filtrate was concentrated by evaporation under reduced pressure. The resulting crude crystalline solid was purified by column chromatography through silica gel using a mixture of hexane and ethyl acetate as the eluent, initially using a gradient of the two solvents starting with a 1: 1 by volume mixture and changing to a final 3:2 by volume mixture to give 2.67 g (yield 52%) of the title compound as a solid having a melting point of 87° to 89° C.

Workup

  1. stirringthe reaction mixture was stirred at room temperature for a further 4 hours
  2. filtrationThe reaction mixture was then filtered
  3. concentrationthe filtrate was concentrated by evaporation under reduced pressure
  4. customThe resulting crude crystalline solid was purified by column chromatography through silica gel using
  5. additiona mixture of hexane and ethyl acetate as the eluent

Sources & evidence

ORD record
ord-00eebc89a5a44f749cc8c1c577d1a41d
Source dataset
uspto-grants-1998_04
Patent number
US05736487

Reaction notes

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