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

HRID 24723

Reaction equation

HRID 24723 reaction equation
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]

Participants

6

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent2×

Procedure

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+)

Workup

  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)

Sources & evidence

ORD record
ord-b4dc9b02a77c414a895c085f1167af81
Source dataset
uspto-grants-2005_02
Patent number
US06855843B2

Linked notes

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