2-Methyl-2-thiopseudourea → 2-Fluoro-4-methoxybenzoic acid diaminomethylene hydrazide

HRID 553626Notes

Reaction equation

HRID 553626 reaction equation
[F:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([NH:6][NH2:7])=[O:5].CS[C:16](=[NH:18])[NH2:17].[OH-].[Na+]>O>[NH2:17][C:16](=[N:7][NH:6][C:4](=[O:5])[C:3]1[CH:8]=[CH:9][C:10]([O:12][CH3:13])=[CH:11][C:2]=1[F:1])[NH2:18]

Participants

5

Reactant 3

HCID 51422-Methyl-2-thiopseudoureaHCID 14798Sodium HydroxideHCID 157020782-Fluoro-4-methoxybenzohydrazide

Product 1

HCID 671228532-Fluoro-4-methoxybenzoic acid diaminomethylene hydrazideYield 42.4%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 4.26 g (23.15 mmol) of 2-fluoro-4-methoxybenzoic acid hydrazide in water (100 mL) are added 12.9 g (46.3 mmol) of S-methylpseudothiourea and 1.9 g (46.3 mmol) of sodium hydroxide pellets. The reaction is stirred at room temperature for 7 d. The reaction mixture is filtered and washed with water (50 mL). The solid is dried under reduced pressure at 40° C., then melted at 220° C. to give 2.22 g (9.82 mmol) of 2-fluoro-4-methoxybenzoic acid diaminomethylene hydrazide. Yield: 42%, ES-MS: m/z. The solid is melted at 220° C. to give 1.735 g (8.34 mmol) of 5-(2-fluoro-methoxyphenyl)-4H-[1,2,4]triazol-3-ylamine. Yield 36%, ES-MS: m/z 209 [M+H].

Workup

  1. filtrationThe reaction mixture is filtered
  2. washwashed with water (50 mL)
  3. customThe solid is dried under reduced pressure at 40° C.

Sources & evidence

ORD record
ord-54d43948d09345e48be1bad5b0bccca1
Source dataset
uspto-grants-2011_11
Patent number
US08048899B2

Reaction notes

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