Ethanamine, 2-fluoro-, hydrochloride → 6-bromo-N-(2-fluoroethyl)benzo[d]thiazol-2-amine

HRID 1965854Notes

Reaction equation

HRID 1965854 reaction equation
[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7](Cl)[S:8][C:4]=2[CH:3]=1.Cl.[F:13][CH2:14][CH2:15][NH2:16]>CO>[Br:1][C:2]1[CH:11]=[CH:10][C:5]2[N:6]=[C:7]([NH:16][CH2:15][CH2:14][F:13])[S:8][C:4]=2[CH:3]=1

Participants

4

Reactant 2

HCID 9995Ethanamine, 2-fluoro-, hydrochlorideHCID 20498716-Bromo-2-chlorobenzothiazole

Product 1

HCID 592830696-bromo-N-(2-fluoroethyl)benzo[d]thiazol-2-amineYield 54.5%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
120 °C

Procedure

A mixture of 6-bromo-2-chlorobenzo[d]thiazole (248 mg, 1 mmol), 2-fluoroethanamine hydrochloride (200 mg, 2 mmol), and TEA (303 mg, 3 mmol) in 3 mL MeOH was heated at 120° C. in a microwave reactor for 20 min. After cooling to rt, the mixture was concentrated and chromatographed (6% to 60% EtOAc in hexane) to afford 6-bromo-N-(2-fluoroethyl)benzo[d]thiazol-2-amine as a white solid (150 mg, 54%). MS (ESI) m/z 276.9 (M+H+).

Workup

  1. temperatureAfter cooling to rt
  2. concentrationthe mixture was concentrated
  3. customchromatographed (6% to 60% EtOAc in hexane)

Sources & evidence

ORD record
ord-bab51b05f12148e58ceca492e0dfb04b
Source dataset
uspto-grants-2013_04
Patent number
US08420052B2

Reaction notes

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