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

HRID 704033Notes

Reaction equation

HRID 704033 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[N:12]=[C:11]([S:13]([NH2:16])(=[O:15])=[O:14])[S:10][N:9]=1.S(Cl)(Cl)=O.[CH:21]([N:23]1[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1)=O>>[N:23]1([CH:21]=[N:16][S:13]([C:11]2[S:10][N:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[CH3:1])[N:12]=2)(=[O:15])=[O:14])[CH2:28][CH2:27][O:26][CH2:25][CH2:24]1

Participants

4

Reactant 3

HCID 20417N-FormylmorpholineHCID 24386Thionyl ChlorideHCID 141831333-(2-Methylphenyl)-1,2,4-thiadiazole-5-sulfonamide

Product 1

HCID 54556514N-(4-Morpholinylmethylene)-3-(2-methylphenyl)-1,2,4-thiadiazole-5-sulfonamide

Procedure

To a solution of 3.5 g of 3-(2-methylphenyl)-1,2,4-thiadiazole-5-sulfonamide in 18 ml of N-formylmorpholine at -5° C. was added 5 ml of thionyl chloride. The resulting mixture was stirred for 3 hours at room temperature, then poured into ice water and stirred for 30 minutes. The solid was collected, washed with water and sucked dry. The solid was then triturated with ether, ether/hexane (1:1) and hexane successively. The product was dried (P2O5) to give 4.52 g of solid, m.p. 151°-153° C.

Workup

  1. stirringstirred for 30 minutes
  2. customThe solid was collected
  3. washwashed with water
  4. customsucked dry
  5. customThe solid was then triturated with ether, ether/hexane (1:1) and hexane successively
  6. dry with materialThe product was dried (P2O5)

Sources & evidence

ORD record
ord-435680c1b2024ec4bc47a97c1d71c554
Source dataset
uspto-grants-1991_01
Patent number
US04985450

Reaction notes

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