Chlorosulfonic acid → Methyl N-[6-(chlorosulfonyl)-1H-benzimidazol-2-yl]carbamate

HRID 382445

Reaktionsgleichung

Reaktionsgleichung von HRID 382445
[C:1]([NH:5][C:6]1[NH:7][C:8]2[CH:14]=[CH:13][CH:12]=[CH:11][C:9]=2[N:10]=1)([O:3][CH3:4])=[O:2].[Cl:15][S:16](O)(=[O:18])=[O:17]>>[Cl:15][S:16]([C:13]1[CH:12]=[CH:11][C:9]2[N:10]=[C:6]([NH:5][C:1]([O:3][CH3:4])=[O:2])[NH:7][C:8]=2[CH:14]=1)(=[O:18])=[O:17]

Komponenten

3

Edukt 2

HCID 24638Chlorosulfonic acidHCID 25429Carbendazim

Produkt 1

HCID 15124047Methyl N-[6-(chlorosulfonyl)-1H-benzimidazol-2-yl]carbamateAusbeute 78 %

Versuchsvorschrift

A solution of 2-carbomethoxyamino-benzimidazole (5.0 g, 0.026 mole) in chlorosulfonic acid (35.00 mL) was stirred at 0° C. for 30 minutes and at room temperature for 3 hours. The resulting dark colored reaction mixture was poured into an ice-water mixture (200 mL), and stirred at room temperature for 30 minutes. The resulting precipitate was filtered and washed with cold water (500 mL). The solid was dried overnight under high vacuum in a desiccator over NaOH pellets to give 5-chlorosulfonyl-2-carbomethoxyamino-benzimidazole (5.9 g, 78%) as a gray powder. 1H NMR (DMSO-d6) d: 3.89 (s, 3H), 7.55 (d, J=8.4 Hz, 1H), 7.65 (d, J=8.4 Hz, 1H), 7.88 (s, 1H). (German Patent DE 3826036).

Aufarbeitung

  1. filtrationThe resulting precipitate was filtered
  2. washwashed with cold water (500 mL)
  3. dry with materialThe solid was dried overnight under high vacuum in a desiccator over NaOH pellets

Quellen und Nachweise

ORD-Eintrag
ord-698d6c42712448d5acd6a7e0ce1a0d94
Quelldatensatz
uspto-grants-2001_10
Patentnummer
US06310080B1

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