Ethanimidic acid, ethyl ester, hydrochloride (1:1) → HCID 15045511, compound

HRID 2107663Notes

Reaction equation

HRID 2107663 reaction equation
Cl.[C:2](=[NH:7])(OCC)[CH3:3].[I:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2N)=[CH:11][CH:10]=1>C(O)C>[I:8][C:9]1[CH:14]=[CH:13][C:12]([N:15]2[C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=3[N:7]=[C:2]2[CH3:3])=[CH:11][CH:10]=1

Participants

4

Reactant 2

HCID 2724290Ethanimidic acid, ethyl ester, hydrochloride (1:1)HCID 15045510N-(4-iodophenyl)1,2-diaminobenzene

Product 1

HCID 15045511HCID 15045511, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Ethyl acetimidate hydrochloride (6.757 g, 54.9 mmol) was added to a suspension of N-(4-iodophenyl)-1,2-diaminobenzene (6.812 g, 22.0 mmol) in absolute ethanol (30 ml) at room temperature. After 2 hours, 50 ml of ice cold 2N aqueous sodium hydroxide was added and the product was extracted into ethyl acetate (2×100 ml). The extracts were washed with water (3×100 ml), dried (MgSO4) and concentrated under reduced pressure to give 1-(4-iodophenyl)-2-methylbenzimidazole, 6.695 g as a white solid, m.p. 136°-7° C.

Workup

  1. extractionthe product was extracted into ethyl acetate (2×100 ml)
  2. washThe extracts were washed with water (3×100 ml)
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-bd33114482db43a5b6d94964de097297
Source dataset
uspto-grants-1990_06
Patent number
US04935430

Reaction notes

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