2-Amino-4-hydroxybenzothiazole → 2-Amino-4-diethylphosphonomethyloxybenzothiazole

HRID 970713

Reaction equation

HRID 970713 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([OH:11])[C:5]=2[N:6]=1.[H-].[Na+].FC(S(O[CH2:22][P:23]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:24])(=O)=O)(F)F>CN(C=O)C>[NH2:1][C:2]1[S:3][C:4]2[CH:10]=[CH:9][CH:8]=[C:7]([O:11][CH2:22][P:23]([O:28][CH2:29][CH3:30])([O:25][CH2:26][CH3:27])=[O:24])[C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 240572-Amino-4-hydroxybenzothiazoleHCID 24758Sodium hydrideHCID 11833487(Diethoxyphosphoryl)methyl trifluoromethanesulfonate

Product 1

HCID 542778482-Amino-4-diethylphosphonomethyloxybenzothiazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-amino-4-hydroxybenzothiazole (1 mmole) and NaH (1.3 mmole) in DMF (5 L) was stirred at 0° C. for 10 min, and then treated with diethylphosphonomethyl trifluoromethylsulfonate (1.2 mmole). After being stirred at room temperature for 8 h, the reaction was subjected to extraction and chromatography to give 2-amino-4-diethylphosphonomethyloxybenzothiazole as an oil.

Workup

  1. stirringAfter being stirred at room temperature for 8 h
  2. extractionthe reaction was subjected to extraction and chromatography

Sources & evidence

ORD record
ord-e00f547c64814cb39b27f09bdc7eda2b
Source dataset
uspto-grants-2007_12
Patent number
US07312219B2

Linked notes

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