Hydrazine hydrate (1:1) → HCID 13958753, compound

HRID 255920Notes

Reaction equation

HRID 255920 reaction equation
[F:1]/[CH:2]=[C:3](\[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])/[CH2:4][N:5]1[C:9](=[O:10])C2=CC=CC=C2C1=O.[OH2:26].NN>C(O)C>[C:3]([O:26][C:9]([NH:5][CH2:4]/[C:3](/[CH2:16][O:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=1[Cl:25])=[CH:2]/[F:1])=[O:10])([CH3:16])([CH3:4])[CH3:2]

Participants

4

Reactant 2

HCID 24654Hydrazine hydrate (1:1)HCID 13958752HCID 13958752, compound

Product 1

HCID 13958753HCID 13958753, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of (Z)-1-fluoro-2-(2',4'-dichlorophenoxy) methyl-3-phthalimidopropene (0.67 g) and hydrazine hydrate (0.13 g) in ethanol (20 ml) is refluxed for 3 hours. The ethanol is evaporated, the residue extracted with ether and the ether solution washed with dilute aqueous sodium hydroxide, then with water, dried and evaporated. The residue is treated with di-tert-butyl dicarbonate (0.44 g), chloroform (20 ml) and water (6 ml), with added sodium chloride (1 g), for 1.5 hours at reflux to give (Z)-N-t-butyloxycarbonyl-2-(2',4'-dichlorophenoxy)methyl-3-fluoroallylamine. Pure colorless needles (0.43 g) are obtained by silica chromatography using 15% EtOAC in light petroleum as eluant. Cleavage of the butyloxycarbonyl group (HCl/ether) gave (Z)-2-(2',4'-dichlorophenoxy)methyl-3-fluoroallylamine as its hydrochloride salt; colorless needles (0.30 g; 59% yield); mp 135°-136° C.

Workup

  1. customThe ethanol is evaporated
  2. extractionthe residue extracted with ether
  3. washthe ether solution washed with dilute aqueous sodium hydroxide
  4. dry with materialwith water, dried
  5. customevaporated
  6. additionThe residue is treated with di-tert-butyl dicarbonate (0.44 g), chloroform (20 ml) and water (6 ml), with added sodium chloride (1 g), for 1.5 hours
  7. temperatureat reflux

Sources & evidence

ORD record
ord-b5281789b5b144ad80ba67c98a10c677
Source dataset
uspto-grants-1987_10
Patent number
US04699928

Reaction notes

Loading…