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

HRID 2351363Notes

Reaction equation

HRID 2351363 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-678f9b358cf24517badbe49b67b1738c
Source dataset
uspto-grants-1989_10
Patent number
US04873239

Reaction notes

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