Diisopropylamine → HCID 178457748, compound

HRID 18621Notes

Reaction equation

HRID 18621 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:5]2[NH:6][C:7]([C:9](Cl)(Cl)Cl)=[N:8][C:4]=2[CH:3]=1.[CH:15]([NH:18][CH:19]([CH3:21])[CH3:20])([CH3:17])[CH3:16].C([O-])(O)=[O:23].[Na+]>C1COCC1.O>[CH:15]([N:18]([CH:19]([CH3:21])[CH3:20])[C:9]([C:7]1[NH:6][C:5]2[CH:13]=[CH:14][C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=1)=[O:23])([CH3:17])[CH3:16]

Participants

6

Reactant 3

HCID 7912DiisopropylamineHCID 516892Sodium BicarbonateHCID 178477904HCID 178477904, compound

Product 1

HCID 178457748HCID 178457748, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 500.0 mg (1.85 mmol) 5-Chloro-2-trichloromethyl-1H-benzoimidazole in 20 mL THF was added slowly to a mixture of 286 μl (2.04 mmol) diisopropyl-amine and 1.55 g (18.5 mmol, 10 equivalents) NaHCO3 in 70 mL THF and 20 mL water. The reaction mixture was stirred for 2 h at RT. The organic solvent was evaporated. The formed crystalline material was filtered off and treated once with about 50 mL of a saturated NaHCO3-solution under ultrasonic conditions. The crystalline residue was filtered off again and washed twice with 20 mL water. Drying under reduced pressure at 35° C. gave pure 5-Chloro-1H-benzoimidazole-2-carboxylic acid diisopropylamide in form of a light brown crystalline solid.

Workup

  1. customThe organic solvent was evaporated
  2. filtrationThe formed crystalline material was filtered off
  3. additiontreated once with about 50 mL of a saturated NaHCO3-solution under ultrasonic conditions
  4. filtrationThe crystalline residue was filtered off again
  5. washwashed twice with 20 mL water
  6. customDrying under reduced pressure at 35° C.

Sources & evidence

ORD record
ord-11b7e1b587b24149a996c26f3b6cd29a
Source dataset
uspto-grants-2010_06
Patent number
US07741341B2

Reaction notes

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