Sodium Hydroxide → HCID 178484362, compound

HRID 1073814Notes

Reaction equation

HRID 1073814 reaction equation
[SH:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.[OH-].[Na+].[CH3:10][N:11]([CH3:16])[C:12](=[NH:15])[CH2:13]Cl>C(O)C>[CH3:10][N:11]([CH3:16])[C:12]([CH2:13][S:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1)=[NH:15]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 426331Ethanimidamide, 2-chloro-N,N-dimethyl-HCID 178418558HCID 178418558, compound

Product 1

HCID 178484362HCID 178484362, compoundYield 53.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

In 30 ml of ethanol was suspended 2.25 g of 2,5-dimercapto-1,3,4-thiadiazole, and 30 ml of 1N-sodium hydroxide solution was added to the suspension. The mixture was stirred at room temperature for 30 minutes. To the mixture was added 2.36 g of N,N-dimethylchloroacetamidine. The mixture was stirred at room temperature for an hour and concentrated under reduced pressure. The precipitating crystals were collected by filtration and washed with cold water and then a (1:1) mixture of methanol and ethyl ether to obtain 1.87 g of 2-(N,N-dimethylamidinomethylthio)-5-mercapto-1,3,4-thiadiazole as colorless crystals (mp 95°-97° C.).

Workup

  1. additionwas added to the suspension
  2. stirringThe mixture was stirred at room temperature for an hour
  3. concentrationconcentrated under reduced pressure
  4. filtrationThe precipitating crystals were collected by filtration
  5. washwashed with cold water
  6. additiona (1:1) mixture of methanol and ethyl ether

Sources & evidence

ORD record
ord-a9b698dfb69a4a9794909e1eeef5c81b
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

Loading…