Chloroform → 1-Sulfonylurea

HRID 1161613Notes

Reaction equation

HRID 1161613 reaction equation
[S:1](=[N:4][C:5]([NH2:7])=[O:6])(=[O:3])=[O:2].NCCC1C=CC([S:17]([NH2:20])(=[O:19])=[O:18])=CC=1.C(Cl)(Cl)Cl.C1(N=C=[N:33][CH:34]2CCCCC2)CCCCC1>C(#N)C.C(=S)=S>[S:1](=[N:4][C:5]([NH2:7])=[O:6])(=[O:3])=[O:2].[S:17]([N:33]=[C:34]=[S:1])(=[O:19])(=[O:18])[NH2:20]

Participants

8

Reactant 4

HCID 6212ChloroformHCID 10868DicyclohexylcarbodiimideHCID 1696824-(2-Aminoethyl)benzenesulfonamide2×HCID 118190831-Sulfonylurea

Product 2

HCID 118190831-SulfonylureaHCID 86594597Sulfamoyl-isothiocyanate

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 6348Carbon DisulfideSolvent

Procedure

A sulfonylurea derivative (SUNCS) is synthesized in preparation for making another sulfonylurea-containing initiator polymer. The preparation of SUNCS is achieved according to the synthetic scheme as illustrated in FIG. 3. 4-(2-Amino-ethyl)benzenesulfonamide (AEBS) is first dissolved in acetonitrile (or chloroform). In step 1 the AEBS solution is reacted with carbon disulfide (CS2) and dicyclohexylcarbodiimide (DCC). Dicyclohexylurea (DCU) product is removed from sulfamoyl-isothiocyanate (S-NCS) by filtration. The solvents are then removed to give the S-NCS intermediate. In step 2 the S-NCS, cyclohexyl isocyanate, and tetrabutylammonium bromide (TBAB) are placed in a glass vessel with tetrahydrofuran (THF) and the mixture is stirred under an inert dry atmosphere during the slow addition of sodium hydride (NaH). The SUNCS product (Compound IV, also shown in Table I) is then isolated and purified by flash chromatography.

Workup

  1. additioncontaining initiator polymer
  2. customThe preparation of SUNCS
  3. customDicyclohexylurea (DCU) product is removed from sulfamoyl-isothiocyanate (S-NCS) by filtration
  4. customThe solvents are then removed

Sources & evidence

ORD record
ord-6f2aebfdebdb4212ba54c7876cafc33e
Source dataset
uspto-grants-2010_10
Patent number
US07820158B2

Reaction notes

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