Water → Pyridine-2-carbaldehyde thiosemicarbazone

HRID 1072534Notes

Reaction equation

HRID 1072534 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=O.[NH2:9][NH:10][C:11]([NH2:13])=[S:12].O>C(O)C.O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH:7]=[N:9][NH:10][C:11]([NH2:13])=[S:12]

Participants

5

Reactant 3

HCID 962WaterHCID 142732-PyridinecarboxaldehydeHCID 2723789Thiosemicarbazide

Product 1

HCID 1638753Pyridine-2-carbaldehyde thiosemicarbazone

Reagents, catalysts & solvents 1

HCID 19096565Water ethanolSolvent

Procedure

The corresponding pyridine-2-formaldehyde (23 or 28a-k, 10 mmol) was dissolved in ethanol-water (2:1 v/v, 150 mL). To the solution was added thiosemicarbazide (11 mmol). The solution was stirred for 30 min at ambient temperature. After addition of water (50 mL), the reaction mixture was stirred vigorously for 2 h at room temperature. The yellow precipitate was collected by filtration, washed with ethanol-water (1:4 v/v) and dried in vacuum to afford the corresponding pyridine-2-carboxaldehyde thiosemicarbazone (24, 29a-k). (2-Thiosemicarbazonomethylpyridin-3-yl)carbamic acid 2-bis(2-trimethyl silyl ethyl) phosphonooxy-5-chlorobenzyl ester (24). Following the above procedure, 23 (6.9 g, 12 mmol) gave 24 (4.9 g, 63%) as a yellow solid:

Workup

  1. stirringthe reaction mixture was stirred vigorously for 2 h at room temperature
  2. filtrationThe yellow precipitate was collected by filtration
  3. washwashed with ethanol-water (1:4 v/v)
  4. customdried in vacuum

Sources & evidence

ORD record
ord-27b108fdcba64dd39e122b6691d0eb2a
Source dataset
uspto-grants-2005_06
Patent number
US06911460B2

Reaction notes

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