HCID 53772768, compound → HCID 53832899, compound

HRID 970719Notes

Reaction equation

HRID 970719 reaction equation
[CH2:1]([O:3][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH:17]=[O:18])=[CH:13][C:12]=1[N+:19]([O-])=O)([O:6][CH2:7][CH3:8])=[O:5])[CH3:2].[H][H]>CO.[Pd]>[CH2:7]([O:6][P:4]([CH2:9][O:10][C:11]1[CH:16]=[CH:15][C:14]([CH2:17][OH:18])=[CH:13][C:12]=1[NH2:19])([O:3][CH2:1][CH3:2])=[O:5])[CH3:8]

Participants

5

Reactant 2

HCID 53772768HCID 53772768, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 53832899HCID 53832899, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

A solution of 2-diethylphosphonomethyloxy-5-formylnitrobenzene (1 mmole) in methanol (5 mL) was treated with 10% palladium on carbon (0.05 mmole) under 1 atmosphere of hydrogen at room temperature for 12 h. Filtration followed by evaporation gave 2-diethylphosphonomethyloxy-5-hydroxymethylaniline which was subjected to Step B of Example 36 followed by Step D of Example 34 to give 2-amino-7-hydroxymethyl-6-thiocyanato-4-phosphonomethoxybenzothiazole (39.1). mp 181–184° C. Anal. Calcd. for C10H10N3O5PS2+0.35H2O: C, 33.97; H, 3.05; N, 11.88. Found: C, 33.76; H, 2.66; N, 11.61.

Workup

  1. filtrationFiltration
  2. customfollowed by evaporation

Sources & evidence

ORD record
ord-1ad844a45fb24b9abf4811554ba002f4
Source dataset
uspto-grants-2007_12
Patent number
US07312219B2

Reaction notes

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