Water → HCID 178512678, compound

HRID 1155775Notes

Reaction equation

HRID 1155775 reaction equation
[N+]([O-])(O)=O.[NH2:5][C:6]([NH2:8])=[NH:7].[H-].[Na+].Cl[C:12]1[S:16][N:15]=[C:14]([CH2:17][Cl:18])[N:13]=1.O>CN(C)C=O>[Cl:18][CH2:17][C:14]1[N:13]=[C:12]([NH:7][C:6]([NH2:8])=[NH:5])[S:16][N:15]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10481Guanidine NitrateHCID 24758Sodium hydrideHCID 3326105-Chloro-3-(chloromethyl)-1,2,4-thiadiazole

Product 1

HCID 178512678HCID 178512678, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Guanidine nitrate (244 g.) was slurried in dimethylformamide (500 ml., dried over molecular sieve) and sodium hydride paste (58 g. of a 63% w/w dispersion in oil) was added over 30 minutes with external cooling in an acetone/solid CO2 bath to maintain the internal temperature at 25°-30°. The mixture was stirred for 30 minutes at 25° then cooled to 20°. 5-Chloro-3-chloromethyl-1,2,4-thiadiazole (84.5 g.) was added at 20°-25° over 20 minutes with external cooling at 5°-10°. The mixture was stirred for 20 minutes at 25° then poured into water (5000 ml.) and extracted with ethyl acetate (2×5000 ml.). The combined upper layers were extracted with 2 N HCl (2×500 ml.) and the combined acid extracts were basified with 2 N NaOH. The product was filtered off, washed with water, sucked dry and then dried over P2O5 at 1 m.m. to give 3-chloromethyl-5-guanidino-1,2,4-thiadiazole.

Workup

  1. additionof a 63% w/w dispersion in oil) was added over 30 minutes
  2. temperaturewith external cooling in an acetone/solid CO2 bath
  3. temperatureto maintain the internal temperature at 25°-30°
  4. temperaturethen cooled to 20°
  5. temperaturewith external cooling at 5°-10°
  6. stirringThe mixture was stirred for 20 minutes at 25°
  7. extractionextracted with ethyl acetate (2×5000 ml.)
  8. extractionThe combined upper layers were extracted with 2 N HCl (2×500 ml.)
  9. filtrationThe product was filtered off
  10. washwashed with water
  11. customsucked dry
  12. dry with materialdried over P2O5 at 1 m

Sources & evidence

ORD record
ord-4d404ecba19e489f8f024c2c8c14a1fe
Source dataset
uspto-grants-1982_06
Patent number
US04332949

Reaction notes

Loading…