Hexane → N-(1-Methoxy-2-methylpropylidene)-3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

HRID 845463Notes

Reaction equation

HRID 845463 reaction equation
[Cl: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.CCCCCC.[C:23](OC)(OC)([O:27][CH3:28])[CH:24]([CH3:26])[CH3:25]>>[CH3:28][O:27][C:23](=[N:16][S:13]([C:11]1[S:10][N:9]=[C:8]([C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Cl:1])[N:12]=1)(=[O:14])=[O:15])[CH:24]([CH3:26])[CH3:25]

Participants

4

Reactant 3

HCID 8058HexaneHCID 404951,1,1-Trimethoxy-2-methylpropaneHCID 141831363-(2-Chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

Product 1

HCID 54055981N-(1-Methoxy-2-methylpropylidene)-3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide

Procedure

A mixture of 2.9 g of 3-(2-chlorophenyl)-1,2,4-thiadiazole-5-sulfonamide in 11 ml of trimethyl orthoisobutyrate was warmed to about 85° with an oil bath. After 2.5 hours the solution was cooled to room temperature, whereupon a precipitate formed. Hexane (25 ml) was added to insure complete precipitation. The solid was filtered, washed with hexane and vacuum dried (P2O5) to give 3.08 g of solid, m.p. 75°-76°.

Workup

  1. temperaturewas warmed to about 85° with an oil bath
  2. customformed
  3. customprecipitation
  4. filtrationThe solid was filtered
  5. washwashed with hexane and vacuum
  6. dry with materialdried (P2O5)

Sources & evidence

ORD record
ord-249588fe09e048bfa3a7604ea08b0d4e
Source dataset
uspto-grants-1988_07
Patent number
US04758578

Reaction notes

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