Acetone → 3-[Allyl-(5-chloro-2-methoxy-benzenesulfonyl)-amino]-4-allyloxy-benzoic acid methyl ester

HRID 641332Notes

Reaction equation

HRID 641332 reaction equation
[CH2:1](Br)[CH:2]=[CH2:3].C(=O)([O-])[O-].[K+].[K+].[CH3:11][O:12][C:13](=[O:34])[C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[C:16]([NH:21][S:22]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[O:32][CH3:33])(=[O:24])=[O:23])[CH:15]=1.[CH3:35][C:36]([CH3:38])=O>>[CH3:11][O:12][C:13](=[O:34])[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:1][CH:2]=[CH2:3])=[C:16]([N:21]([CH2:38][CH:36]=[CH2:35])[S:22]([C:25]2[CH:30]=[C:29]([Cl:31])[CH:28]=[CH:27][C:26]=2[O:32][CH3:33])(=[O:23])=[O:24])[CH:15]=1

Participants

5

Reactant 4

HCID 180AcetoneHCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 667891293-(5-Chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester

Product 1

HCID 667889743-[Allyl-(5-chloro-2-methoxy-benzenesulfonyl)-amino]-4-allyloxy-benzoic acid methyl esterYield 100%

Conditions

Temperature
60 °C

Procedure

Allyl bromide (195 mg, 1.63 mmol) and potassium carbonate (372 mg, 2.69 mmol) was added to a solution of 3-(5-chloro-2-methoxy-benzenesulfonylamino)-4-hydroxy-benzoic acid methyl ester (example 30, step 1; 200 mg, 0.538 mmol) in acetone, and the reaction mixture was stirred at 60° C. for 16 h. After cooling, insoluble material was filtered off and the filtrate evaporated to produce 3-[allyl-(5-chloro-2-methoxy-benzenesulfonyl)-amino]-4-allyloxy-benzoic acid methyl ester (243 mg, 100%). Orange solid, MS (ISP)=452.1 (M+H)+.

Workup

  1. temperatureAfter cooling
  2. filtrationinsoluble material was filtered off
  3. customthe filtrate evaporated

Sources & evidence

ORD record
ord-3288c7a981f644519fdbe1b6d5b9a469
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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