Dimethyl Sulfate → 2-{[4-(Dimethylamino)phenyl]diazenyl}-6-methoxy-3-methyl-1,3-benzothiazol-3-ium methyl sulfate

HRID 611447Notes

Reaction equation

HRID 611447 reaction equation
[CH3:1][O:2][C:3]1[CH:22]=[CH:21][C:6]2[N:7]=[C:8]([N:10]=[N:11][C:12]3[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=3)[S:9][C:5]=2[CH:4]=1.[S:23]([O:28]C)([O:26][CH3:27])(=[O:25])=[O:24]>ClC1C=CC=CC=1>[CH3:27][O:26][S:23]([O-:28])(=[O:25])=[O:24].[CH3:20][N:18]([CH3:19])[C:15]1[CH:14]=[CH:13][C:12]([N:11]=[N:10][C:8]2[S:9][C:5]3[CH:4]=[C:3]([O:2][CH3:1])[CH:22]=[CH:21][C:6]=3[N+:7]=2[CH3:27])=[CH:17][CH:16]=1

Participants

4

Reactant 2

HCID 6497Dimethyl SulfateHCID 773904-((6-Methoxybenzothiazol-2-yl)azo)-N,N-dimethylaniline

Product 1

HCID 1611062-{[4-(Dimethylamino)phenyl]diazenyl}-6-methoxy-3-methyl-1,3-benzothiazol-3-ium methyl sulfate

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of [4-(6-methoxy-benzothiazol-2-ylazo)phenyl]-dimethyl-amine (Example 4b, 0.75 g, 2.40 mmol) and dimethyl sulfate (0.50 mL, 5.28 mmol) in 15 mL of chlorobenzene was heated under nitrogen at 70° C. for 3 hours. The solution was cooled and solid formed. The mixture was filtered, the solid was washed with diethyl ether and recrystallized from ethanol to give the title compound as a dark blue-black solid, mp 206-207° C., dec.

Workup

  1. temperatureThe solution was cooled
  2. customsolid formed
  3. filtrationThe mixture was filtered
  4. washthe solid was washed with diethyl ether
  5. customrecrystallized from ethanol

Sources & evidence

ORD record
ord-50b4ea20d9b148bca48d75e7c2081bce
Source dataset
uspto-grants-1999_12
Patent number
US06001331

Reaction notes

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