Triethylamine → 2-(4,5-Dichloro-imidazol-2-yl)-5-amino-1,3,4-thiadiazole

HRID 1164377Notes

Reaction equation

HRID 1164377 reaction equation
[NH2:1][NH:2][C:3]([NH2:5])=[S:4].C(N(CC)CC)C.[Cl:13][C:14]1[N:15]=[C:16]([C:20](Cl)(Cl)Cl)[NH:17][C:18]=1[Cl:19]>C(O)C>[Cl:13][C:14]1[N:15]=[C:16]([C:20]2[S:4][C:3]([NH2:5])=[N:2][N:1]=2)[NH:17][C:18]=1[Cl:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 2723789ThiosemicarbazideHCID 124825734,5-Dichloro-2-(trichloromethyl)-1H-imidazole

Product 1

HCID 1357554472-(4,5-Dichloro-imidazol-2-yl)-5-amino-1,3,4-thiadiazoleYield 76.5%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

9.1 g (0.1 mol) of thiosemicarbazide and 40.4 g (0.4 mol) of triethylamine were stirred in 200 ml of ethanol until a clear solution had formed. 25.4 g (0.1 mol) of 4,5-dichloro-2-trichloromethyl-imidazole were added to this solution incrementally at 0°-5° C., while stirring. The mixture was stirred for a further 1 hour with cooling, for 1 hour at room temperature and for 1 hour at 50° C. After cooling, the amine-hydrochloride was filtered off and the filtrate was evaporated in vacuo. The residue was treated with water, the mixture was acidified with hydrochloric acid and the product was filtered off, washed with water and dried. 18 g (76.5% of theory) of 2-(4,5-dichloro-imidazol-2-yl)-5-amino-1,3,4-thiadiazole were obtained. Melting point: 147° C. (with decomposition) (from ethyl acetate/ligroin).

Workup

  1. customhad formed
  2. stirringThe mixture was stirred for a further 1 hour
  3. temperatureAfter cooling
  4. filtrationthe amine-hydrochloride was filtered off
  5. customthe filtrate was evaporated in vacuo
  6. additionThe residue was treated with water
  7. filtrationthe product was filtered off
  8. washwashed with water
  9. customdried

Sources & evidence

ORD record
ord-594b65e652024119a5719c7ea4daf10d
Source dataset
uspto-grants-1983_01
Patent number
US04369186

Reaction notes

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