Benzoic acid, 2-(isocyanatosulfonyl)-, methyl ester → Benzoic acid, 2-(((((6-chloro-3,4-dihydro-4-methyl-3-oxopyrazinyl)amino)carbonyl)amino)sulfonyl)-, methyl ester

HRID 1381467

反応式

HRID 1381467 の反応式
[NH2:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Cl:8])[N:7]=1.[C:11]([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[S:21]([N:24]=[C:25]=[O:26])(=[O:23])=[O:22])([O:13][CH3:14])=[O:12]>ClCCCl>[Cl:8][C:6]1[N:7]=[C:2]([NH:1][C:25]([NH:24][S:21]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][C:15]=2[C:11]([O:13][CH3:14])=[O:12])(=[O:23])=[O:22])=[O:26])[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1

参加物

4

反応物 2

HCID 156281Benzoic acid, 2-(isocyanatosulfonyl)-, methyl esterHCID 130629753-amino-5-chloro-1-methyl-2(1H)-pyrazinone

生成物 1

HCID 189318Benzoic acid, 2-(((((6-chloro-3,4-dihydro-4-methyl-3-oxopyrazinyl)amino)carbonyl)amino)sulfonyl)-, methyl ester

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

実験手順

To a mixture of 3-amino-5-chloro-1-methyl-2(1H)-pyrazinone (0.40 g, 0.0025 mol) in anhydrous 1,2-dichloroethane (4 mL) under nitrogen was added a solution of 2-carbomethoxybenzenesulfonyl isocyanate (0.84 g, 0.0035 mol) in anhydrous 1,2-dichloromethane (3 mL). The mixture was heated at reflux for 2 hours. The solvent was rotary evaporated, and the residue was purified by chromatography on a column of silica gel using a solvent mixture of 1:1 hexanes-acetone containing a little acetic acid as eluant. Rotary evaporation of the appropriate fractions left 0.34 g of methyl 2-[[(6-chloro-3,4-dihydro-4-methyl-3-oxo-2-pyrazinylamino)carbonylamino]sulfonyl]benzoate as a crystalline powder melting at 173°-176° C.

後処理

  1. temperatureThe mixture was heated
  2. temperatureat reflux for 2 hours
  3. customthe residue was purified by chromatography on a column of silica gel using
  4. additiona solvent mixture of 1:1 hexanes-acetone containing a little acetic acid as eluant
  5. customRotary evaporation of the appropriate fractions
  6. waitleft 0.34 g of methyl 2-[[(6-chloro-3,4-dihydro-4-methyl-3-oxo-2-pyrazinylamino)carbonylamino]sulfonyl]benzoate as a crystalline powder melting at 173°-176° C.

出典と根拠

ORDレコード
ord-1d16adcee93b46dfb7cbe875e7a498ae
出典データセット
uspto-grants-1989_02
特許番号
US04802908

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