N-Formylmorpholine → N-(4-Morpholinylmethylene)-3-phenyl-1,2,4-thiadiazole-5-sulfonamide

HRID 2351362Notes

Reaction equation

HRID 2351362 reaction equation
S(Cl)(Cl)=O.[C:5]1([C:11]2[N:15]=[C:14]([S:16]([NH2:19])(=[O:18])=[O:17])[S:13][N:12]=2)[CH:10]=[CH:9][CH:8]=[CH:7][CH:6]=1.[CH:20]([N:22]1[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1)=O>>[N:22]1([CH:20]=[N:19][S:16]([C:14]2[S:13][N:12]=[C:11]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:15]=2)(=[O:18])=[O:17])[CH2:27][CH2:26][O:25][CH2:24][CH2:23]1

Participants

4

Reactant 3

HCID 20417N-FormylmorpholineHCID 24386Thionyl ChlorideHCID 141831323-Phenyl-1,2,4-thiadiazole-5-sulfonamide

Product 1

HCID 53678661N-(4-Morpholinylmethylene)-3-phenyl-1,2,4-thiadiazole-5-sulfonamide

Procedure

Thionyl chloride (4.5 ml) was added dropwise to 3.0 g of 3-phenyl-1,2,4-thiadiazole-5-sulfonamide in 15 ml of dry N-formylmorpholine at -5°. The resulting mixture was stirred at room temperature for 3 hours, poured into ice water and stirred for 15 minutes. The solids were collected, washed with water, dried, triturated with ether, washed with hexane and dried (in vacuo, P2O5). Recrystallization from benzene/hexane gave 1.1. g of solid, m.p. 185°-187°.

Workup

  1. stirringstirred for 15 minutes
  2. customThe solids were collected
  3. washwashed with water
  4. customdried
  5. customtriturated with ether
  6. washwashed with hexane
  7. dry with materialdried (in vacuo, P2O5)
  8. customRecrystallization from benzene/hexane
  9. customgave 1.1

Sources & evidence

ORD record
ord-70e1234bf9104a3b86dd661b01e6831c
Source dataset
uspto-grants-1989_10
Patent number
US04873239

Reaction notes

Loading…