Dichloromethane → 5-(2-Methylsulphonylaminomethyl-prop-2-yl)-2-(4-pyridinyl)-benzimidazole

HRID 1639134Notes

Reaction equation

HRID 1639134 reaction equation
[NH2:1][CH2:2][C:3]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[NH:12][C:8]=2[CH:7]=1)([CH3:5])[CH3:4].C(N(CC)CC)C.ClCCl.[S:31](Cl)([CH3:34])(=[O:33])=[O:32]>O>[CH3:34][S:31]([NH:1][CH2:2][C:3]([C:6]1[CH:20]=[CH:19][C:9]2[N:10]=[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)[NH:12][C:8]=2[CH:7]=1)([CH3:4])[CH3:5])(=[O:33])=[O:32]

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 141530275-(2-Aminomethylprop-2-yl)-2-(4-pyridinyl)-benzimidazole

Product 1

HCID 141530455-(2-Methylsulphonylaminomethyl-prop-2-yl)-2-(4-pyridinyl)-benzimidazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To 2.0 g. of the 5-(2-aminomethylprop-2-yl)-2-(4-pyridinyl)-benzimidazole (prepared in Example 1) and 830 mg. triethylamine in 50 ml. dry dichloromethane are added dropwise, while cooling with ice water, 953 mg. mesyl chloride. The reaction mixture is stirred for 10 minutes and then 20 ml. water are added thereto. After filtering off with suction, washing with water and dichloromethane and recrystallising from water/ethanol (2:1 v/v), there are obtained 2.0 g. (85% of theory) of the title compound as a hydrate in the form of yellowish crystals which sinter above 130° C., again crystalline above 150° C. and then melt at 215°-216° C.

Workup

  1. filtrationAfter filtering off with suction
  2. washwashing with water and dichloromethane
  3. customrecrystallising from water/ethanol (2:1 v/v), there
  4. customare obtained 2.0 g

Sources & evidence

ORD record
ord-3f30f5acf22b419493bb21763ca2fb6e
Source dataset
uspto-grants-1989_11
Patent number
US04882342

Reaction notes

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