Hydrochloric Acid → HCID 86679532, compound

HRID 1776580Notes

Reaction equation

HRID 1776580 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][C:9]([NH:12][S:13]([CH3:16])(=[O:15])=[O:14])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].Br[CH2:18][CH:19]1[CH2:21][CH2:20]1.C([O-])([O-])=O.[K+].[K+].Cl>CC#N>[CH:19]1([CH2:18][N:12]([C:9]2[CH:10]=[CH:11][C:2]([OH:1])=[C:3]([CH:8]=2)[C:4]([O:6][CH3:7])=[O:5])[S:13]([CH3:16])(=[O:15])=[O:14])[CH2:21][CH2:20]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 81503BromomethylcyclopropaneHCID 838180HCID 838180, compound

Product 1

HCID 86679532HCID 86679532, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a solution of methyl 2-hydroxy-5-(methylsulfonamido)benzoate (6.8 g, 27.72 mmol) in CH3CN (200 ml), (bromomethyl)cyclopropane (5.62 g, 41.58 mmol) and K2CO3 (7.66 g, 55.4 mmol) were added, and the reaction was stirred at RT for 4 days. The reaction mixture was poured into ice-water (400 ml), acidified with HCl 36% (pH=1) and extracted with EtOAc. The organic layer was dried over Na2SO4 and evaporated to dryness. The resulting crude was purified by chromatography on silica gel column (petroleum ether:EtOAc=4:1) affording methyl 5-(N-(cyclopropylmethyl)methylsulfonamido)-2-hydroxybenzoate (6 g, 20.32 mmol, 73.3% yield).

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe organic layer was dried over Na2SO4
  3. customevaporated to dryness
  4. customThe resulting crude was purified by chromatography on silica gel column (petroleum ether:EtOAc=4:1)

Sources & evidence

ORD record
ord-c24156bd182043f7804ac2c53ac69851
Source dataset
uspto-grants-2016_02
Patent number
US09265768B2

Reaction notes

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