Triethylamine → HCID 178512424, compound

HRID 1073813Notes

Reaction equation

HRID 1073813 reaction equation
[SH:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1.C(N(CC)CC)C.Cl.Cl[CH2:17][C:18]([NH2:20])=[NH:19]>CN(C=O)C>[C:18]([CH2:17][S:1][C:2]1[S:3][C:4]([SH:7])=[N:5][N:6]=1)(=[NH:19])[NH2:20]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27769572-Chloroacetamidine monohydrochlorideHCID 178418558HCID 178418558, compound

Product 1

HCID 178512424HCID 178512424, compoundYield 36.7%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 1.50 g of 2,5-dimercapto-1,3,4-thiadiazole and 4.2 ml of triethylamine in 30 ml of DMF was added 1.29 g of α-chloroacetamidine hydrochloride at room temperature under stirring. Further, the mixture was stirred for 2.5 hours at room temperature and concentrated under reduced pressure. The residue was subjected to a column chromatography on silica gel (100 g), eluting with a (4:1) mixture of acetonitrile and water. The pertinent fractions were collected and concentrated under reduced pressure, and the concentrate was subjected to a column chromatography on XAD-II (450 ml) being washed with water, and eluted with 10% aqueous ethanol. After concentrating, the precipitating crystals were filtered to give 755mg of 2-amidinomethylthio-5-mercapto-1,3,4-thiadiazole as colorless crystals, mp: 184°-187° C.

Workup

  1. stirringFurther, the mixture was stirred for 2.5 hours at room temperature
  2. concentrationconcentrated under reduced pressure
  3. washeluting with a (4:1) mixture of acetonitrile and water
  4. customThe pertinent fractions were collected
  5. concentrationconcentrated under reduced pressure
  6. washbeing washed with water
  7. washeluted with 10% aqueous ethanol
  8. concentrationAfter concentrating
  9. filtrationthe precipitating crystals were filtered

Sources & evidence

ORD record
ord-7931e3afdf424e2a9c8b6c6f4e805a7c
Source dataset
uspto-grants-1990_11
Patent number
US04971963

Reaction notes

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