Chloroform → 1-Sulfonylurea

HRID 1161613ノート

反応式

HRID 1161613 の反応式
[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]

参加物

8

反応物 4

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

生成物 2

HCID 118190831-SulfonylureaHCID 86594597Sulfamoyl-isothiocyanate

試薬・触媒・溶媒 2

HCID 6342Acetonitrile溶媒HCID 6348Carbon Disulfide溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6f2aebfdebdb4212ba54c7876cafc33e
出典データセット
uspto-grants-2010_10
特許番号
US07820158B2

反応ノート

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