Methanesulfonamide → HCID 72613057, compound

HRID 2181136Notes

Reaction equation

[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([O:17][CH3:18])[C:6](=[O:16])[CH:7]=[C:8]1[C:12](=O)[O:11]C(C)(C)[O:9]1.[CH3:24][S:25]([NH2:28])(=[O:27])=[O:26]>>[Cl:1][C:2]1[CH:22]=[C:21]([F:23])[CH:20]=[CH:19][C:3]=1[CH2:4][N:5]([O:17][CH3:18])[C:6](=[O:16])[CH:7]=[C:8]([OH:9])[C:12]([NH:28][S:25]([CH3:24])(=[O:27])=[O:26])=[O:11]

Participants

Reactant 2

HCID 72879Methanesulfonamide

HCID 73855585N-(2-Chloro-4-fluorobenzyl)-2-(2,2-dimethyl-5-oxo-[1,3]-dioxolan-4-ylidene)-N-methoxy-acetamide

Product 1

HCID 72613057HCID 72613057, compoundYield 45.8%

Procedure

Reaction of N-(2-chloro-4-fluoro-benzyl)-2-(2,2-dimethyl-5-oxo-[1,3]dioxolan-4-ylidene)-N-methoxy-acetamide (0.175 g, 0.51 mmol) with methanesulfonamide (0.073 g, 0.77 mmol) as described in the preparation of compound 22 gave 0.089 g (45% yield) of the title amide as a white solid after crystallization from ethyl acetate-hexane; mp=144° C. (decomposition). 1H NMR (400 MHz, CDCl3) δ: 3.36 (3H, s, SO2CH3), 3.71 (3H, s, OCH3), 4.96 (2H, s, NCH2), 6.60 (1H, s, CH), 6.95-7.32 (3H, m, aromatics), 8.96 (1H, broad s, NH). Anal. calcd for C13H14ClFN2O6S: C, 41.00; H, 3.70; N, 7.35; found: C, 41.03; H, 3.61; N, 7.29.

Sources & evidence

ORD record: ord-9ea9b81c60984e4e8e20cdadc77119bf
Source dataset: uspto-grants-2005_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06890942B2

Reaction notes

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