Methanesulfonyl chloride → HCID 86679496, compound

HRID 1776540Notes

Reaction equation

HRID 1776540 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:15]=[CH:16][C:17]=1[O:18][CH3:19])[C:5]([O:7][CH2:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=[O:6].[CH3:20][S:21](Cl)(=[O:23])=[O:22]>Cl>[CH3:19][O:18][C:17]1[CH:16]=[CH:15][C:4]([C:5]([O:7][CH2:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[O:6])=[CH:3][C:2]=1[NH:1][S:21]([CH3:20])(=[O:23])=[O:22]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 54195745Phenylmethyl 3-amino-4-methoxybenzoate

Product 1

HCID 86679496HCID 86679496, compoundYield 63.2%

Reagents, catalysts & solvents 1

HCID 313Hydrochloric AcidSolvent

Procedure

Benzyl 3-amino-4-methoxybenzoate (300 mg, 1.17 mmol) was dissolved in Py (5 ml). Methanesulfonyl chloride (140 mg, 1.22 mmol) was added at 0° C. and under Argon atmosphere. The mixture was stirred at RT for 1 hour, then it was diluted with HCl 1N and extracted with EtOAc. The organic phase was washed with HCl 1M, dried over Na2SO4 and concentrated under vacuum to give benzyl 4-methoxy-3-(methylsulfonamido)benzoate (247 mg, 63.2% yield).

Workup

  1. extractionextracted with EtOAc
  2. washThe organic phase was washed with HCl 1M
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-2a69283b5dea4a0ba6a6c79067302f0c
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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