Sulfuric Acid → HCID 178496990, compound

HRID 1898342Notes

Reaction equation

HRID 1898342 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[CH:15]=[C:16]([OH:23])[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1.OS(O)(=O)=O.[N+:29]([O-])([O-:31])=[O:30].[K+]>>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[NH:9][C:10]1[NH:14][C:13]2[C:15]([N+:29]([O-:31])=[O:30])=[C:16]([OH:23])[C:17]([C:19]([O:21][CH3:22])=[O:20])=[CH:18][C:12]=2[N:11]=1

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24434Potassium NitrateHCID 178496988HCID 178496988, compound

Product 1

HCID 178496990HCID 178496990, compoundYield 88.7%

Procedure

To a mixture of methyl 2-[(2,6-dichlorophenyl)amino]-6-hydroxy-1H-benzimidazole-5-carboxylate (0.050 g, 0.142 mmol) and conc. H2SO4 (2.0 mL) was added KNO3 (0.014 g, 0.142 mmol) at 10-15° C. The reaction mass was stirred for 30 minutes at the same temperature. The reaction mass was quenched in water and filtered off to afford 0.050 g of the desired product. 1HNMR (DMSO-d6): δ 3.91 (s, 3H), 7.43 (t, J=8.1 Hz, 1H), 7.61-7.77 (m, 3H), 10.80 (s, 1H), 11-12.00 (s, 2H); MS [M+H]+: 397.02.

Workup

  1. customThe reaction mass was quenched in water
  2. filtrationfiltered off

Sources & evidence

ORD record
ord-d9d0b16edfe648b1b01bafa861ecf990
Source dataset
uspto-grants-2013_08
Patent number
US08519149B2

Reaction notes

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