2-Amino-6-methoxybenzothiazole → HCID 71519730, compound

HRID 529204Notes

Reaction equation

HRID 529204 reaction equation
[CH:1]([C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])=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-:31])([O:29][CH3:30])[O:27][CH3:28].ClCCl.CCOC(C)=O>C1(C)C=CC=CC=1>[CH3:28][O:27][P:26]([CH:1]([NH:23][C:21]1[S:22][C:18]2[CH:17]=[C:16]([O:15][CH3:14])[CH:25]=[CH:24][C:19]=2[N:20]=1)[C:3]1[CH:4]=[CH:5][C:6]([OH:13])=[C:7]([CH:12]=1)[C:8]([O:10][CH3:11])=[O:9])([O:29][CH3:30])=[O:31]

Participants

6

Reactant 4

HCID 156302-Amino-6-methoxybenzothiazoleHCID 14363598Methyl 5-FormylsalicylateHCID 21226138Dichloromethane ethylacetateHCID 21884954Dimethylphosphite

Product 1

HCID 71519730HCID 71519730, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

The mixture of methyl 5-formyl-2-hydroxybenzoate (2) (0.1 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 dimethyl phosphite (0.061 g, 5 mmol) were added, and the reaction mixture was refluxed for 6 hours. The progress of the reaction was monitored by TLC (Dichloromethane:EtOAc 1:9). After completion of the reaction, the solvent was removed under reduced pressure. The combined EtOAc extracts were dried (Na2SO4) and concentrated under reduced pressure to afford a white solid, which was purified by passing through silica gel column using EtOAc:dichloromethane (4:1) as eluent to afford compound (4). The same experimental procedure was adopted for the preparation of the remaining title compounds 5-7, 9-14 and 16-17.

Workup

  1. temperaturethe reaction mixture was refluxed for 6 hours
  2. customAfter completion of the reaction
  3. customthe solvent was removed under reduced pressure
  4. dry with materialThe combined EtOAc extracts were dried (Na2SO4)
  5. concentrationconcentrated under reduced pressure
  6. customto afford a white solid, which
  7. customwas purified

Sources & evidence

ORD record
ord-827f487a07094bf397985fab608ad2f8
Source dataset
uspto-grants-2016_05
Patent number
US09346839B2

Reaction notes

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