Hydrochloric Acid → Dimethyl 5-(methylsulfonamido)isophthalate

HRID 1160443Notes

Reaction equation

HRID 1160443 reaction equation
N[C:2]1([C:12]([O:14][CH3:15])=[O:13])[CH:11]=[CH:10][CH:9]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH2:3]1.[CH3:16][S:17](Cl)(=[O:19])=[O:18].Cl.[N:22]1C=CC=CC=1>>[CH3:16][S:17]([NH:22][C:10]1[CH:11]=[C:2]([C:12]([O:14][CH3:15])=[O:13])[CH:3]=[C:4]([CH:9]=1)[C:5]([O:7][CH3:8])=[O:6])(=[O:19])=[O:18]

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 20454260Dimethyl 3-aminoisophthalate

Product 1

HCID 3711983Dimethyl 5-(methylsulfonamido)isophthalateYield 100%

Conditions

Temperature
50 °C

Procedure

A mixture of dimethyl 3-aminoisophthalate 25.3 g (121 mmol), methanesulfonyl chloride 10 mL (130 mmol) and pyridine (50 mL) was stirred at 50° C. for 4 hours. The reaction solution was poured into a 0.5 N hydrochloric acid (300 mL), and the precipitated solid was collected by filtering, washed with 0.5 N hydrochloric acid and dried under vacuum to give 34.8 g (121 mmol) of the title compound (yield: 100%).

Workup

  1. customthe precipitated solid was collected
  2. filtrationby filtering
  3. washwashed with 0.5 N hydrochloric acid
  4. customdried under vacuum

Sources & evidence

ORD record
ord-dd35fba211984e6892cbf05559f7ad59
Source dataset
uspto-grants-2010_10
Patent number
US07816387B2

Reaction notes

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