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

HRID 462056Notes

Reaction equation

C(N(CC)CC)C.Cl.[C:9]([O:12][CH:13]([CH2:16][O:17][C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[CH2:14][NH2:15])(=[O:11])[CH3:10].[Cl:24][C:25]([Cl:30])([Cl:29])[C:26](N)=[NH:27].CN(C)C=O>O>[ClH:24].[C:9]([O:12][CH:13]([CH2:16][O:17][C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1)[CH2:14][NH:15][C:26](=[NH:27])[C:25]([Cl:30])([Cl:29])[Cl:24])(=[O:11])[CH3:10]

Participants

Conditions

Temperature: 60 °C

Procedure

Triethylamine (0.50 g., 5.0 mmoles) is added in small portions over 10 minutes to a well stirred mixture of 1.23 g. (5.0 mmoles) of 2-acetoxy-3-phenoxy-propylamine hydrochloride and 1.61 g. (10 mmoles) of trichloroacetamidine in 5 ml. of dimethylformamide. The reaction mixture is heated at 60° C. for 2 hours, diluted with water and extracted with benzene. The benzene extract is washed with water, dried over magnesium sulfate, filtered and concentrated. The residue is dissolved in benzene and treated with an excess of ethanolic hydrogen chloride. Concentration to dryness affords N-(2-acetoxy-3-phenoxypropyl) trichloroacetamidine hydrochloride with a m.p. of 70° to 77° C.

Workup

additionmixture of 1.23 g
extractionextracted with benzene
extractionThe benzene extract
washis washed with water
dry with materialdried over magnesium sulfate
filtrationfiltered
concentrationconcentrated
dissolutionThe residue is dissolved in benzene
additiontreated with an excess of ethanolic hydrogen chloride
concentrationConcentration to dryness

Sources & evidence

ORD record: ord-04ec3107b7904c1f8865f7ad8b66703f
Source dataset: uspto-grants-1977_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04065465

Reaction notes

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