2-Aminobenzimidazole → HCID 12429110, compound

HRID 1576518Notes

Reaction equation

HRID 1576518 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][Cl:10].[NH2:11][C:12]1[NH:13][C:14]2[CH:20]=[CH:19][CH:18]=[CH:17][C:15]=2[N:16]=1>S1(CCCC1)(=O)=O.CC(O)C>[Cl-:10].[NH2:11][C:12]1[N:16]([CH2:9][O:8][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=2[Br:1])[C:15]2[CH:17]=[CH:18][CH:19]=[CH:20][C:14]=2[N+:13]=1[CH2:9][O:8][C:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[Br:1]

Participants

5

Reactant 2

HCID 136242-AminobenzimidazoleHCID 21828492HCID 21828492, compound

Product 1

HCID 12429110HCID 12429110, compoundYield 43%

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 31347SulfolaneSolvent2×

Procedure

o-Bromo-α-chloroanisole 15.0 g (0.0679 mol) in 20 ml of sulfolane is added to a solution of 4.50 g (0.0339 mol) of 2-aminobenzimidazole in 40 ml of sulfolane. The mixture turns into a semi-solid mass upon standing for several hours. After standing for 6.75 days at room temperature, the reaction mixture is diluted with 40 ml of 2-propanol, filtered, and the product is washed with 2-propanol. Trituration with ether gives 7.7 g (43%) of a white solid; mp 229°-230°. Recrystallization of 3.5 g of this material from 340 ml of 90% ethanol gives 2.5 g of the named product as a white fluffy solid after drying for 6 hours at 78° (1 mm): mp 236°-237°dec.

Workup

  1. waitupon standing for several hours
  2. filtrationfiltered
  3. washthe product is washed with 2-propanol

Sources & evidence

ORD record
ord-9a3742d7e3d14d8db9f7e75072f351fd
Source dataset
uspto-grants-1976_09
Patent number
US03981886

Reaction notes

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