Methanesulfonyl chloride → HCID 5303011, compound

HRID 1776596Notes

Reaction equation

HRID 1776596 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][C:11]=1[O:12][CH3:13])[C:5]([O:7][CH3:8])=[O:6].[CH3:14][S:15](Cl)(=[O:17])=[O:16]>N1C=CC=CC=1>[CH3:13][O:12][C:11]1[CH:10]=[CH:9][C:4]([C:5]([O:7][CH3:8])=[O:6])=[CH:3][C:2]=1[NH:1][S:15]([CH3:14])(=[O:17])=[O:16]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 2734814Methyl 3-Amino-4-methoxybenzoate

Product 1

HCID 5303011HCID 5303011, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
0 °C

Procedure

A solution of methyl 3-amino-4-methoxybenzoate (prepared in an analogous manner to that described in Scheme 17, Step 1) (2.00 g, 11.04 mmol) in dry pyridine (25 ml) was cooled to 0° C.; methanesulfonyl chloride (1.115 ml, 14.35 mmol) was added drop wise, and the mixture was warmed to RT and stirred for 3 hours. The solvent was evaporated under vacuum, and the residue was partitioned between DCM and HCl 2N. The organic layer was washed with brine and dried over Na2SO4; the solvent was removed; and the residue was triturated with iPr2O to give methyl 4-methoxy-3-(methylsulfonamido)benzoate (2.6 g, 10.03 mmol, 91% yield, MS/ESI+ 260.1 [MH]+).

Workup

  1. temperaturethe mixture was warmed to RT
  2. customThe solvent was evaporated under vacuum
  3. customthe residue was partitioned between DCM and HCl 2N
  4. washThe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. customthe solvent was removed
  7. customand the residue was triturated with iPr2O

Sources & evidence

ORD record
ord-dd53c7c1d1934da4bf8e38a3f0cf4bfd
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

Loading…