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

HRID 1984565Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1984565
[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) was added dropwise to a solution of (63a) (10 g, 40 mmol) in CH2Cl2 (500 ml) at −80° C. The mixture was allowed to reach room temperature in 5 h. The reaction mixture was poured on ice and quickly extracted with CH2Cl2. The organic layer was dried over MgSO4 and the solvent was evaporated to dryness which afforded 8.8 g (63%) of desired sulfonyl chloride (63b); mp 133-35° C., 1H NMR (DMSO-d6) 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=3.39 Hz, 1H), 6.77 (d, J=3.39 Hz, 1H), 4.53 (d, J=3.77 Hz, 2H).

Aufarbeitung

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

Quellen und Nachweise

ORD-Eintrag
ord-e691464e15f142ee85c6955bc1ffd3b0
Quelldatensatz
uspto-grants-2009_06
Patentnummer
US07544700B2

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