Acetate → N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride

HRID 462055

Reaction equation

HRID 462055 reaction equation
[Cl:1][CH2:2][CH:3]([OH:12])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1.[Cl:13][C:14]([Cl:19])([Cl:18])[C:15]([NH2:17])=[NH:16].[C:20]([O-])(=[O:22])[CH3:21].C(Cl)(=O)C>O1CCCC1.C(O)(=O)C>[ClH:1].[C:20]([O:12][CH:3]([CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)[CH2:2][NH:16][C:15](=[NH:17])[C:14]([Cl:19])([Cl:18])[Cl:13])(=[O:22])[CH3:21]

Participants

7

Reactant 4

HCID 175AcetateHCID 6367Acetyl chlorideHCID 356082,2,2-TrichloroethanimidamideHCID 943001-Chloro-3-phenoxy-2-propanol

Product 1

HCID 178476389N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of 9.3 g. (0.05 mole) of 1-chloro-2-hydroxy-3-phenoxypropane in 100 ml. of tetrahydrofuran is mixed with a solution of 8.1 g. (0.05 mole) of trichloroacetamidine, also in tetrahydrofuran. The mixture is heated at reflux for 3 hours, and concentrated to an oil, which is taken up in benzene and washed well with water. The benzene layer is dried over magnesium sulfate, filtered, and treated with excess ethanolic hydrogen chloride to provide the crude hydroxy amidine hydrochloride. This is dissolved in glacial acetic acid and converted to the acetate by treatment with 3.5 g. (0.04 mole) of acetyl chloride at room temperature for 3 days. The reaction mixture is evaporated, treated with benzene, evaporated to dryness, and the process repeated once more with benzene, twice with toluene and twice with petroleum ether. There is afforded N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride, m.p. 70° to 77° C.

Workup

  1. temperatureThe mixture is heated
  2. temperatureat reflux for 3 hours
  3. concentrationconcentrated to an oil, which
  4. washwashed well with water
  5. dry with materialThe benzene layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. additiontreated with excess ethanolic hydrogen chloride
  8. customto provide the crude hydroxy amidine hydrochloride
  9. customThe reaction mixture is evaporated
  10. additiontreated with benzene
  11. customevaporated to dryness

Sources & evidence

ORD record
ord-3cc1b248ecb84b97b74215c9dbb66d04
Source dataset
uspto-grants-1977_12
Patent number
US04065464

Linked notes

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