Sodium Hydroxide → 2-[(4-Chlorophenyl)sulfonyl-methyl-amino]prop-2-enoic acid

HRID 1479812Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8]([N:11]([CH3:19])[C@@H:12]([CH2:17]O)[C:13]([O:15]C)=[O:14])(=[O:10])=[O:9])=[CH:4][CH:3]=1.[OH-].[Na+]>O1CCOCC1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([S:8]([N:11]([CH3:19])[C:12](=[CH2:17])[C:13]([OH:15])=[O:14])(=[O:9])=[O:10])=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A solution of 3C (8.5 g, 27.6 mmol) in dioxane (20 mL) was added with 20% NaOH aq. solution (30 mL) and the mixture heated at 80° C. for 5 h. The organic solvent was removed under reduced pressure and the aqueous phase acidified with 10% HCl and extracted with CH2Cl2 (3×50 mL). The combined organic phases were dried over Na2SO4 and evaporated under reduced pressure to afford 4C as a pale yellow deliquescent solid (4.3 g, 62% yield). 1HNMR (DMSO, 200 MHz) δ 2.91 (s, 3H), 5.58 (s, 1H), 6.09 (s, 1H), 7.72-7.60 (m, 4H), 13.05 (bs, 1H).

Workup

customThe organic solvent was removed under reduced pressure
extractionextracted with CH2Cl2 (3×50 mL)
dry with materialThe combined organic phases were dried over Na2SO4
customevaporated under reduced pressure

Sources & evidence

ORD record: ord-c5c9e693063f4525a9d7bd62c99e63d6
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409864B2

Reaction notes

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