Bromine → 4-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

HRID 1582106Notes

Reaction equation

HRID 1582106 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([CH:9]2[CH2:14][CH2:13][O:12][CH2:11][CH2:10]2)=[CH:5][C:4]=1[NH:15][C:16]([NH2:18])=[S:17].BrBr>C(Cl)(Cl)Cl>[CH3:1][O:2][C:3]1[C:4]2[N:15]=[C:16]([NH2:18])[S:17][C:5]=2[C:6]([CH:9]2[CH2:10][CH2:11][O:12][CH2:13][CH2:14]2)=[CH:7][CH:8]=1

Participants

4

Reactant 2

HCID 24408BromineHCID 22015747[2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea

Product 1

HCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amineYield 49%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 1.90 g (7.13 mmol) [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea in 50 ml chloroform was added dropwise 0.37 ml (7.22 mmol) bromine and the mixture heated at reflux for 18 hours. The mixture was then concentrated in vacuo. The residue was recrystallised from ethyl acetate to afford 920 mg (49%) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine as a white solid. ES-MS m/e (%): 265 (M+H+, 100).

Workup

  1. temperaturethe mixture heated
  2. temperatureat reflux for 18 hours
  3. concentrationThe mixture was then concentrated in vacuo
  4. customThe residue was recrystallised from ethyl acetate

Sources & evidence

ORD record
ord-09b3ff6583e347f29af5335ec2fd2c3e
Source dataset
uspto-grants-2004_05
Patent number
US06734179B2

Reaction notes

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