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

HRID 982932Notes

Reaction equation

HRID 982932 reaction equation
[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]

Participants

3

Reactant 2

HCID 24638Chlorosulfonic acidHCID 25429Carbendazim

Product 1

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

Procedure

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 grey 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)

Workup

  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

Sources & evidence

ORD record
ord-53958290a12d483d9574807e8418319a
Source dataset
uspto-grants-2005_03
Patent number
US06861539B1

Reaction notes

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