2-Amino-6-methoxybenzothiazole → HCID 71519734, compound

HRID 529205Notes

Reaction equation

HRID 529205 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)C(OC)=O)=O.[CH3:14][O:15][C:16]1[CH:25]=[CH:24][C:19]2[N:20]=[C:21]([NH2:23])[S:22][C:18]=2[CH:17]=1.[P:26]([O-:33])([O:30][CH2:31]C)[O:27][CH2:28]C>C1(C)C=CC=CC=1>[OH:13][C:6]1[CH:7]=[CH:12][C:3]([CH:1]([P:26](=[O:33])([O:30][CH3:31])[O:27][CH3:28])[NH:23][C:21]2[S:22][C:18]3[CH:17]=[C:16]([O:15][CH3:14])[CH:25]=[CH:24][C:19]=3[N:20]=2)=[CH:4][CH:5]=1

Participants

5

Reactant 3

HCID 156302-Amino-6-methoxybenzothiazoleHCID 3780918DiethylphosphiteHCID 14363598Methyl 5-Formylsalicylate

Product 1

HCID 71519734HCID 71519734, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of 4-hydroxybenzaldehyde (2) (0.067 g, 5 mmol) and Mg(ClO4)2 (0.12 g, 5 mol %) was stirred for 10-15 minutes in anhydrous toluene (5 mL), after which time 6-methoxybenzo[d]thiazol-2-amine (1) (0.1 g, 5 mmol) and diethyl phosphite (0.076 g, 5 mmol) were added, and the reaction mixture was refluxed for 3 hours followed by usual workup and chromatographic purification [silica gel:EtOAc-Dichloromethane (8.5:1.5) as eluent] afforded the dimethyl ((4-hydroxyphenyl)((6-methoxybenzo[d]thiazol-2-yl)amino)methyl)phosphonate as colorless solid.

Workup

  1. temperaturethe reaction mixture was refluxed for 3 hours
  2. customfollowed by usual workup and chromatographic purification [silica gel:EtOAc-Dichloromethane (8.5:1.5) as eluent]

Sources & evidence

ORD record
ord-45cbd0c4896740d3bb6caf9020d53187
Source dataset
uspto-grants-2016_05
Patent number
US09346839B2

Reaction notes

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