HCID 18680859, compound → HCID 18681084, compound

HRID 1699643Notes

Reaction equation

HRID 1699643 reaction equation
Cl[S:2]([C:5]1[CH:23]=[CH:22][C:8]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[C:10]([CH3:12])=[N:11][C:7]=2[CH:6]=1)(=[O:4])=[O:3].ClS(C1C=CC2N=C(C)[N:33](CC3C=CC(Cl)=CC=3Cl)C=2C=1)(=O)=O>N>[NH2:33][S:2]([C:5]1[CH:23]=[CH:22][C:8]2[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=3[Cl:21])[C:10]([CH3:12])=[N:11][C:7]=2[CH:6]=1)(=[O:4])=[O:3]

Participants

4

Reactant 2

HCID 18680859HCID 18680859, compoundHCID 186810611-[(2,4-Dichlorophenyl)methyl]-2-methyl-1H-benzimidazole-5-sulfonyl chloride

Product 1

HCID 18681084HCID 18681084, compound

Reagents, catalysts & solvents 1

HCID 222AmmoniaSolvent

Procedure

The mixture of 5-chlorosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole and 6-chlorosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole, which is obtained in Example 285, is immediately processed with a 25% aqueous ammonia (100 ml) for one hour at room temperature. Separation of solids through filtration produced a 1/1 mixture (2.68 g) of 5-aminosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole and 6-aminosulfonyl-1-(2,4-dichlorobenzyl)-2-methylbenzimidazole. 1H-NMR (CD3OD, δ): 2.52 (3/2H, s), 2.54 (3/2H, s), 5.54 (2H, s), 6.55 (1H, d, J=6.9 Hz), 7.17 (1H, d, J=8.0 Hz), 7.52 (1H, s), 7.65-7.78 (2H, m), 7.82 (1/2H, s), 8.11 (1/2H, s).

Workup

  1. customwhich is obtained in Example 285
  2. customSeparation of solids
  3. filtrationthrough filtration

Sources & evidence

ORD record
ord-d2833358b6bc40099478bb76ee81ab87
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

Loading…