Pyridine → methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate

HRID 24723

反応式

HRID 24723 の反応式
N1C=CC=CC=1.[NH2:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1.[CH3:19][N:20]([CH3:25])[S:21](Cl)(=[O:23])=[O:22]>C(Cl)Cl.CN(C1C=CN=CC=1)C>[CH3:19][N:20]([CH3:25])[S:21]([NH:7][C:8]1[CH:17]=[CH:16][C:11]([C:12]([O:14][CH3:15])=[O:13])=[C:10]([Cl:18])[CH:9]=1)(=[O:23])=[O:22]

参加物

6

反応物 3

HCID 1049PyridineHCID 83372Dimethylsulphamoyl chlorideHCID 11839197Methyl 4-Amino-2-chlorobenzoate

生成物 1

HCID 22571711methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒2 回

実験手順

Pyridine (0.4 mL) was added to a solution of methyl 4-amino-2-chlorobenzoate (0.3 g) in CH2Cl2 (10 mL) at 0° C. under N2. N,N-Dimethylsulfamoyl chloride (0.21 mL) was added and the mixture was stirred at room temperature for 16 hours and refluxed for 5 hours. DMAP (0.4 g) was added and the mixture was stirred for 3 hours. The mixture was diluted with CH2Cl2 (100 mL), washed successively with 1N HCl, brine, satd. NaHCO3 and brine, dried and evaporated. The residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3) to give 0.31 g of methyl 4-(N,N-dimethylsulfamoyl)amino-2-chlorobenzoate. ESMS: m/z 293 (MH+)

後処理

  1. temperaturerefluxed for 5 hours
  2. stirringthe mixture was stirred for 3 hours
  3. washwashed successively with 1N HCl, brine
  4. dry with materialNaHCO3 and brine, dried
  5. customevaporated
  6. customThe residue was purified by flash column chromatography (silica gel; eluent: EtOAc/hexane 1:3)

出典と根拠

ORDレコード
ord-b4dc9b02a77c414a895c085f1167af81
出典データセット
uspto-grants-2005_02
特許番号
US06855843B2

関連ノート

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