Methanesulfonyl chloride → HCID 58683717, compound

HRID 1991067Notes

Reaction equation

HRID 1991067 reaction equation
[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[NH2:16])[CH3:2].[CH3:18][S:19](Cl)(=[O:21])=[O:20]>N1C=CC=CC=1>[CH2:1]([O:3][C:4](=[O:17])/[CH:5]=[CH:6]/[C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([Cl:15])=[CH:9][C:8]=1[NH:16][S:19]([CH3:18])(=[O:21])=[O:20])[CH3:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 59128619HCID 59128619, compound

Product 1

HCID 58683717HCID 58683717, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

(E)-3-(2-Amino-4-chloro-5-methoxyphenyl)-acrylic acid ethyl ester (250 mg; 0.98 mmol) in pyridine (2 ml) was treated with methanesulfonyl chloride (0.15 ml; 2 mmol) for 15 min. at room temperature. The reaction mixture was poured on water and extracted with TBME three times. The combined organic phases were evaporated to dryness and purified via chromatography (SiO2; acetone/hexanes 2/8) to yield the title compound as slightly yellow crystals (216 mg; 66%)

Workup

  1. additionThe reaction mixture was poured on water
  2. extractionextracted with TBME three times
  3. customThe combined organic phases were evaporated to dryness
  4. custompurified via chromatography (SiO2; acetone/hexanes 2/8)

Sources & evidence

ORD record
ord-db4a018a9ce742d7a02002f445d6fcd3
Source dataset
uspto-grants-2010_01
Patent number
US07645760B2

Reaction notes

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