Methyl chloroformate → Carbamic acid, [(2-chlorophenyl)sulfonyl]-, methyl ester

HRID 12511

Reaction equation

HRID 12511 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([NH2:11])(=[O:10])=[O:9].C(N(CC)CC)C.Cl[C:20]([O:22][CH3:23])=[O:21]>C(#N)C>[CH3:23][O:22][C:20](=[O:21])[NH:11][S:8]([C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Cl:1])(=[O:10])=[O:9]

Participants

5

Reactant 3

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 814102-Chlorobenzenesulfonamide

Product 1

HCID 4389137Carbamic acid, [(2-chlorophenyl)sulfonyl]-, methyl ester

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 25.0 g 2-chloro-benzenesulfonamide was added 75 mL acetonitrile and 45.2 mL (2.5 eq) triethylamine. The mixture was cooled with an ice bath and 15.1 mL methyl chloroformate was slowly added dropwise. The mixture was stirred overnight at room temperature and concentrated in vacuo. Water was added and de aqueous layer was washed two times with ether. Acidification of the aqueous layer with 2 M HCl led to formation of a white precipitate. The suspension was filtered, the residue was washed with H2O and dried in vacuo to yield 19.1 g of a white solid. 1H NMR (400 MHz, DMSO-d6) δ 3.58 (s, 3H), 7.52-7.61 (m, 1H), 7.62-7.72 (m, 2H), 8.10 (dd, J=8 and 1.5 Hz, 1H), 12.42 (br s, 1H).

Workup

  1. temperatureThe mixture was cooled with an ice bath
  2. concentrationconcentrated in vacuo
  3. additionWater was added and de aqueous layer
  4. washwas washed two times with ether
  5. filtrationThe suspension was filtered
  6. washthe residue was washed with H2O
  7. customdried in vacuo

Sources & evidence

ORD record
ord-ac56c7d916db4ddcb9163798bf19af4e
Source dataset
uspto-grants-2010_06
Patent number
US07728018B2

Linked notes

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