Hydrochloric Acid → HCID 21434093, compound

HRID 2398782Notes

Reaction equation

HRID 2398782 reaction equation
[C:1]([C:3]1[CH:19]=[CH:18][CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH:7]([OH:15])[CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])#[N:2].OO.[ClH:22]>CCOCC>[C:1]([C:3]1[CH:19]=[C:18]([Cl:22])[CH:17]=[CH:16][C:4]=1[O:5][CH2:6][CH:7]([OH:15])[CH2:8][NH:9][C:10]([CH3:14])([CH3:13])[CH2:11][OH:12])#[N:2]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 784Hydrogen PeroxideHCID 21434085HCID 21434085, compound

Product 1

HCID 21434093HCID 21434093, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
45 °C

Procedure

9.7 gm (about 0.037 mol) of 1-(2'-cyano-phenoxy)-2-hydroxy-3-[(1",1"-dimethyl-2"-hydroxy-ethyl)-amino]-propane, prepared as in Example 1, were dissolved in 75 ml of concentrated hydrochloric acid, the solution was heated to 45° C., and then 4.7 gm of an aqueous 30% hydrogen peroxide solution (about 0.038 H2O2) were added dropwise. A strong exothermic reaction ensued, and the temperature of the reaction mixture was kept at 65° C. by exterior cooling. After all of the peroxide had been added, the reaction solution was stirred for 30 minutes at 60°-65° C. and subsequently evaporated to dryness in vacuo. The residue was dissolved in water, the resulting solution was extracted twice with ether, and the aqueous phase was made alkaline with 2N sodium hydroxide. The oily precipitate formed thereby was taken up in ether, and the resulting solution was washed with water, dried and evaporated, leaving 9.3 gm of a solid residue which was recrystallized twice from ethyl acetate by addition of petroleum ether (40°-60° C.). 6.6 gm of the compound of the formula ##STR13## having a melting point of 102°-103° C. were obtained.

Workup

  1. customA strong exothermic reaction
  2. customwas kept at 65° C. by exterior cooling
  3. customsubsequently evaporated to dryness in vacuo
  4. dissolutionThe residue was dissolved in water
  5. extractionthe resulting solution was extracted twice with ether
  6. customThe oily precipitate formed
  7. washthe resulting solution was washed with water
  8. customdried
  9. customevaporated

Sources & evidence

ORD record
ord-20f36eaaf88d497d9143956bd4042736
Source dataset
uspto-grants-1977_05
Patent number
US04025646

Reaction notes

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