2,6-Lutidine → HCID 66779832, compound

HRID 2405628Notes

Reaction equation

HRID 2405628 reaction equation
[C:1](Cl)(=[O:10])[O:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:12]1([C:18]2[NH:19][C:20]3[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=3[N:22]=2)[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.N1C(C)=CC=CC=1C>O1CCCC1>[CH2:3]([O:2][C:1]([N:19]1[C:20]2[CH:26]=[CH:25][CH:24]=[CH:23][C:21]=2[N:22]=[C:18]1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[O:10])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 3

HCID 79372,6-LutidineHCID 10387Benzyl chloroformateHCID 128552-Phenylbenzimidazole

Product 1

HCID 66779832HCID 66779832, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

In a nitrogen atmosphere, 107 g of benzyl chlorocarbonate was added dropwise to a solution of 97 g of 2-phenylbenzimidazole and 107 g of 2,6-lutidine in 700 g of tetrahydrofuran, which was heated and stirred at 50° C. for 20 hours. After ordinary aqueous work-up, the insoluble was filtered off. The filtrate was concentrated, washed with hexane, and dried, obtaining 118 g of 1-benzyloxycarbonyl-2-phenylbenzimidazole (yield 72%).

Workup

  1. temperaturewas heated
  2. filtrationAfter ordinary aqueous work-up, the insoluble was filtered off
  3. concentrationThe filtrate was concentrated
  4. washwashed with hexane
  5. customdried

Sources & evidence

ORD record
ord-5682cf080f4e4f76959b106efaa0065c
Source dataset
uspto-grants-2014_08
Patent number
US08808964B2

Reaction notes

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