Butyl isocyanate → N-(Butylaminocarbonyl)-2[5-(methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide

HRID 255822Notes

Reaction equation

HRID 255822 reaction equation
[CH3:1][S:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[CH2:14][S:15]([NH2:18])(=[O:17])=[O:16])=[N:5][N:4]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:25]([N:29]=[C:30]=[O:31])[CH2:26][CH2:27][CH3:28]>CC(=O)CC>[CH2:25]([NH:29][C:30]([NH:18][S:15]([CH2:14][C:9]1[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=1[C:6]1[O:7][C:3]([S:2][CH3:1])=[N:4][N:5]=1)(=[O:17])=[O:16])=[O:31])[CH2:26][CH2:27][CH3:28]

Participants

5

Reactant 3

HCID 8110Butyl isocyanateHCID 11430Potassium CarbonateHCID 139587772-[5-(Methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamide

Product 1

HCID 13958780N-(Butylaminocarbonyl)-2[5-(methylthio)-1,3,4-oxadiazol-2-yl]benzenemethanesulfonamideYield 92.8%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A suspension containing 16 g of the sulfonamide of Example 3, 7.7 g of potassium carbonate and 6.7 g of n-butylisocyanate in 130 of 2-butanone was refluxed for 4 hours, then stirred overnight at room temperature. After concentrating the mixture in vacuo, the residue was diluted with about 150 ml of water and the solution was washed 1×100 ml of ethyl ether. The aqueous layer was acidified with concentrated hydrochloric acid (red to litmus paper) and the resulting suspension was filtered, then suction-dried overnight to give 20 g of the subject compound; m.p. 156°-159°. IR (nujol): 1680 cm-1 (C=O).

Workup

  1. temperaturewas refluxed for 4 hours
  2. concentrationAfter concentrating the mixture in vacuo
  3. additionthe residue was diluted with about 150 ml of water
  4. washthe solution was washed 1×100 ml of ethyl ether
  5. filtrationthe resulting suspension was filtered
  6. customsuction-dried overnight

Sources & evidence

ORD record
ord-1459a8fd00e345b2a3df8e6a0745cf3a
Source dataset
uspto-grants-1987_10
Patent number
US04699649

Reaction notes

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