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

HRID 1593707Notes

Reaction equation

HRID 1593707 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 min. and at room temperature for 3 hr. The resulting dark colored reaction mixture was carefully poured into an ice-water mixture (200 mL) and stirred at room temperature for 30 min. The resulting precipitate was filtered and washed throughly with cold water (500 ml). The solid was dried overnight under high vacuum in a desiccator over NaOH pallets to yield the desired compound (5.9 g. 78%) as a grey powder. 1H NMR (DMSO-d6) 3.89 (s, 3H), 7.55 (d, 1H, J=8.4 Hz.) 7.65 (d, 1H, J=8.4 Hz), 7.88 (s, 1H).

Workup

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

Sources & evidence

ORD record
ord-adec403f24fd4e3295945742dee6a9c0
Source dataset
uspto-grants-2007_11
Patent number
US07297793B2

Reaction notes

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