Potassium Carbonate → 2-Bromomethyl-6-methoxybenzothiazole

HRID 581048Notes

Reaction equation

HRID 581048 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[SH:10].[Br:11][CH2:12][C:13](Br)=O.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[Br:11][CH2:12][C:13]1[S:10][C:3]2[CH:4]=[C:5]([O:8][CH3:9])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 61147Bromoacetyl bromideHCID 2355092-Amino-5-methoxybenzene-1-thiol

Product 1

HCID 107063232-Bromomethyl-6-methoxybenzothiazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

7.75 g (50 mmol) of 2-amino-5-methoxy-thiophenol are dissolved in 150 ml methylene chloride and 14.1 g (70 mmol) of bromoacetylbromide are added whilst cooling with ice. Then the mixture is heated for 1 hour to reflux temperature. After cooling solid potassium carbonate is added until foaming ceases, the mixture is filtered and the filtrate is evaporated down. The evaporation residue is purified by column chromatography on neutral aluminium oxide (eluant: petroleum ether/ethyl acetate=3:1). Yield: 6.8 g (52.7 of theory), Melting point: 90-91° C.

Workup

  1. temperaturewhilst cooling with ice
  2. temperatureThen the mixture is heated for 1 hour
  3. temperatureto reflux temperature
  4. additionis added
  5. filtrationthe mixture is filtered
  6. customthe filtrate is evaporated down
  7. customThe evaporation residue is purified by column chromatography on neutral aluminium oxide (eluant: petroleum ether/ethyl acetate=3:1)

Sources & evidence

ORD record
ord-c4912c173d144ac6b3e261b9afa35f1c
Source dataset
uspto-grants-1999_07
Patent number
US05919807

Reaction notes

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