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

HRID 968538Notes

Reaction equation

HRID 968538 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].Br.CS(C)=O>C(O)(=O)C>[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

5

Reactant 3

HCID 260Hydrogen BromideHCID 679Dimethyl SulfoxideHCID 22015747[2-Methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea

Product 1

HCID 220157354-Methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-yl-amine

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 1 [2-methoxy-5-(tetrahydro-pyran-4-yl)-phenyl]-thiourea (XI) in acetic acid is added hydrobromic acid, and stirring continued for about 30 min at 80° C. DMSO is then added dropwise and the reaction mixture stirred for a further 30 min at 80° C. The product (XII) 4-methoxy-7-(tetrahydro-pyran-4-yl)-benzothiazol-2-ylamine is isolated by conventional means.

Workup

  1. stirringthe reaction mixture stirred for a further 30 min at 80° C

Sources & evidence

ORD record
ord-58071eab15a4470e83f4aaa19074f653
Source dataset
uspto-grants-2007_12
Patent number
US07304058B2

Reaction notes

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