Hydrochloric Acid → HCID 12283309, compound

HRID 1155291Notes

Reaction equation

HRID 1155291 reaction equation
[C:1]([CH2:3][CH:4]1[O:9][C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5]1)#[N:2].[CH2:14]([OH:16])[CH3:15].[ClH:17]>C(OCC)C>[ClH:17].[O:9]1[C:8]2[CH:10]=[CH:11][CH:12]=[CH:13][C:7]=2[O:6][CH2:5][CH:4]1[CH2:3][C:1](=[NH:2])[O:16][CH2:14][CH3:15]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 2675312-(2,3-Dihydro-1,4-benzodioxin-2-yl)acetonitrile

Product 1

HCID 12283309HCID 12283309, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

17.5 g (0.10 mole) 2-cyanomethyl-1,4-benzodioxane, prepared as described by Augstein, et al., J. Med. Chem. 8: 446 (1965), was dissolved in a mixture containing 7 g ethanol and 50 ml diethyl ether. 4.5 g (0.15 moles) of dry HCl was bubbled though the mixture, which was then capped. The mixture was allowed to stand at 5° C. for 4 days, followed by 3 days at room temperature. The crude product imidate hydrochloride (IV) precipitated out and was harvested by filtration, and washed with 100 ml ether, followed by 3×100 ml portions of methylene chloride. The solid was then purified by thin layer chromatography using 10% methanol in chloroform as a developing solvent. The product has an Rf value of 0.7-0.8; starting material moves farther in this solvent system, and none was present in the crude product. The yield of product was 15.3 g, as the hydrochloride, or 59% yield.

Workup

  1. dissolution8: 446 (1965), was dissolved in a mixture
  2. customwas then capped
  3. waitfollowed by 3 days at room temperature
  4. customThe crude product imidate hydrochloride (IV) precipitated out and
  5. filtrationwas harvested by filtration
  6. washwashed with 100 ml ether
  7. customThe solid was then purified by thin layer chromatography

Sources & evidence

ORD record
ord-7f61a0c5c2ae431ab5e889b67c205e12
Source dataset
uspto-grants-1981_11
Patent number
US04301171

Reaction notes

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