2-Aminobenzimidazole → HCID 12429112, compound

HRID 1576519Notes

Reaction equation

HRID 1576519 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[Cl:11][CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Br:21]>S1(CCCC1)(=O)=O.CC(O)C>[Cl-:11].[NH2:1][C:2]1[N:6]([CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Br:21])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N+:3]=1[CH2:12][O:13][C:14]1[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=1[Br:21]

Participants

5

Reactant 2

HCID 136242-AminobenzimidazoleHCID 21828493HCID 21828493, compound

Product 1

HCID 12429112HCID 12429112, compound

Reagents, catalysts & solvents 2

HCID 3776IsopropanolSolventHCID 31347SulfolaneSolvent

Procedure

A mixture of 1.00 g (0.00745 mol) of 2-aminobenzimidazole and 1.91 g (0.00745 mol) of 2-bromo-4-chlorophenyl chloromethyl ether in 5 ml of sulfolane is allowed to stand at room temperature for 22 hours. A solid precipitate forms within 5 minutes of mixing the two reagents. The product mixture is diluted with 10 ml of cold 2-propanol, and filtered, and the solid product is washed with two portions of cold 2-propanol. Drying in vacuo over P2O5 gives 2.28 g (100% crude yield) of the product as a white solid: mp 230° sinters, melts 233°-234° dec. The product is dissolved in 400 ml of hot 95% ethanol, and the solution is concentrated to a volume of 200 ml. The solution is allowed to cool slowly while precipitating a white floculant solid which is isolated from the chilled mixture to give 1.11 g (49% yield) of the named product: mp 235°-236°dec.

Workup

  1. additionA solid precipitate forms within 5 minutes of mixing the two reagents
  2. filtrationfiltered
  3. washthe solid product is washed with two portions of cold 2-propanol
  4. dry with materialDrying in vacuo over P2O5

Sources & evidence

ORD record
ord-1f30bcf75bf74543a0bdca1fb9bfa548
Source dataset
uspto-grants-1976_09
Patent number
US03981886

Reaction notes

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