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

HRID 641333Notes

Reaction equation

HRID 641333 reaction equation
[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH2:11][CH:12]=[CH2:13])=[C:6]([N:14]([CH2:27][CH:28]=[CH2:29])[S:15]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[O:25][CH3:26])(=[O:17])=[O:16])[CH:5]=1>C1(C)C=CC=CC=1.[H-].[C-]#[O+].C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.[Cl-].[Ru+2]>[CH3:1][O:2][C:3](=[O:30])[C:4]1[CH:9]=[CH:8][C:7]([O:10][CH:11]=[CH:12][CH3:13])=[C:6]([N:14]([S:15]([C:18]2[CH:23]=[C:22]([Cl:24])[CH:21]=[CH:20][C:19]=2[O:25][CH3:26])(=[O:17])=[O:16])[CH:27]=[CH:28][CH3:29])[CH:5]=1

Participants

4

Reactant 1

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

Product 1

HCID 667888873-[(5-Chloro-2-methoxy-benzenesulfonyl)-propenyl-amino]-4-[(propenyl)oxy]-benzoic acid methyl esterYield 73%

Reagents, catalysts & solvents 2

HCID 86892Einecs 241-051-0Catalyst2×HCID 1140TolueneSolvent

Procedure

A solution of 3-[allyl-(5-chloro-2-methoxy-benzenesulfonyl)-amino]-4-allyloxy-benzoic acid methyl ester (243 mg, 0.537 mmol) and carbonylchlorohydrotris(triphenylphosphine)-ruthenium (15 mg, 16 μmol) in toluene (2.6 mL) was stirred at 95° C. for 16 h, then another portion of carbonylchlorohydrotris(triphenylphosphine)ruthenium (27 mg, 25 μmol) was added, and stirring was continued over 48 h, then the solvent was evaporated. Chromatography (SiO2, heptane-ethyl acetate gradient) furnished 3-[(5-chloro-2-methoxy-benzenesulfonyl)-propenyl-amino]-4-[(propenyl)oxy]-benzoic acid methyl ester (177 mg, 73%). Light red oil, MS (ISP)=452.1 (M+H)+.

Workup

  1. customthe solvent was evaporated

Sources & evidence

ORD record
ord-c9e3808ad3f547e0b82b0ba515a87f2f
Source dataset
uspto-grants-2010_04
Patent number
US07696200B2

Reaction notes

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