Triethylamine → HCID 12042347, compound

HRID 840770Notes

Reaction equation

HRID 840770 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[CH:11][CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][CH2:15][CH3:16].C([N:23](CC)CC)C.[CH3:28][S:29](Cl)(=[O:31])=[O:30]>C(Cl)Cl>[Cl:1][C:2]1[CH:20]=[CH:19][CH:18]=[CH:17][C:3]=1[CH2:4][N:5]1[C:9]2[CH:10]=[C:11]([NH:23][S:29]([CH3:28])(=[O:31])=[O:30])[CH:12]=[CH:13][C:8]=2[N:7]=[C:6]1[CH2:14][CH2:15][CH3:16]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 949881HCID 949881, compound

Product 1

HCID 12042347HCID 12042347, compoundYield 62.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-(2-Chlorobenzyl)-2-n-propylbenzimidazole (150 mg) and triethylamine (61 mg) are dissolved in methylene chloride (3 ml). Methanesulfonyl chloride (70 mg) is added to the mixture solution at room temperature, stirred for 1 hour, and then washed with diluted hydrochloric acid. After it is washed with water, it is dried and the solvent is removed through evaporation under reduced pressure. The solid residue is filtered using ether, and 1-(2-chlorobenzyl)-6-mesylamino-2-n-propylbenzimidazole (124 mg) is obtained. 1H-NMR, (CDCl3—CD3OD, δ): 0.94 (3H, t, J=7.5 Hz), 1.76 (2H, m), 2.71 (2H, t, J=7.5 Hz), 2.81 (3H, s), 5.36 (2H, s), 6.40 (1H, d, J=7.5 Hz), 6.98-7.22 (4H,m), 7.40 (1H, d, J=7.5 Hz), 7.59 (1H, d, J=7.5 Hz).

Workup

  1. washwashed with diluted hydrochloric acid
  2. washAfter it is washed with water, it
  3. customis dried
  4. customthe solvent is removed through evaporation under reduced pressure
  5. filtrationThe solid residue is filtered

Sources & evidence

ORD record
ord-8ee6abf2823f4cc29e5f8f33781687f0
Source dataset
uspto-grants-2002_04
Patent number
US06369092B1

Reaction notes

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