Chlorosulfonic acid → 5-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chloride

HRID 1869265Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1869265
[Cl:1][S:2]([OH:5])(=O)=[O:3].[Cl:6][C:7]1[CH:21]=[CH:20][C:10]([C:11]([NH:13][CH2:14][C:15]2[S:16][CH:17]=[CH:18][CH:19]=2)=[O:12])=[CH:9][CH:8]=1>C(Cl)Cl>[Cl:6][C:7]1[CH:8]=[CH:9][C:10]([C:11]([NH:13][CH2:14][C:15]2[S:16][C:17]([S:2]([Cl:1])(=[O:5])=[O:3])=[CH:18][CH:19]=2)=[O:12])=[CH:20][CH:21]=1

Komponenten

4

Edukt 2

HCID 24638Chlorosulfonic acidHCID 7222864-chloro-N-(thiophen-2-ylmethyl)benzamide

Produkt 1

HCID 27357135-((4-Chlorobenzamido)methyl)thiophene-2-sulfonyl chlorideAusbeute 63 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel2×

Versuchsvorschrift

Chlorosulfonic acid (20.1 ml, 198 mmol) in CH2Cl2 (80 ml) is added dropwise to a solution of 1a (10 g, 40 mmol) in CH2Cl2 (500 ml) at −80° C. The mixture is allowed to reach room temperature in 5 h. The reaction mixture is poured on ice and quickly extracted with CH2Cl2. The organic layer is dried over MgSO4 and the solvent is evaporated to dryness which affords 8.8 g (63%) of desired sulfonyl chloride 1b; mp 133-35° C., 1H NMR (DMSO) δ 9.21 (t, J=6.4 Hz, 1H), 7.87 (d, J=8.67 Hz, 2H), 7.53 (d, J=8.67 Hz, 2H), 6.91 (d, J=3.9 Hz, 1H), 6.77 (d, J=3.39 Hz, 1H), 4.53 (d, J=3.77 Hz, 2H).

Aufarbeitung

  1. additionThe reaction mixture is poured on ice
  2. extractionquickly extracted with CH2Cl2
  3. dry with materialThe organic layer is dried over MgSO4
  4. customthe solvent is evaporated to dryness which

Quellen und Nachweise

ORD-Eintrag
ord-38aae4b85edc4e0ca4557297d3862d86
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07638538B1

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