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

HRID 24723

반응식

HRID 24723 반응식
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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매2회

실험 절차

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+)

후처리

  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)

출처 및 근거

ORD 기록
ord-b4dc9b02a77c414a895c085f1167af81
출처 데이터셋
uspto-grants-2005_02
특허 번호
US06855843B2

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