Isopropylamine → HCID 22765392, compound

HRID 1112235Notes

Reaction equation

HRID 1112235 reaction equation
[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]1[O:8][CH2:7]1.[CH:19]([NH2:22])([CH3:21])[CH3:20]>C(O)C>[Cl:1][C:2]1[CH:12]=[C:11]([NH:13][C:14]([N:16]([CH3:18])[CH3:17])=[O:15])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][CH:6]([OH:8])[CH2:7][NH:22][CH:19]([CH3:21])[CH3:20]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 22765390HCID 22765390, compound

Product 1

HCID 22765392HCID 22765392, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A solution of 40 g of 1-[o-chloro-p-(N',N'-dimethyl-ureido)-phenoxy]-2,3-epoxy-propane and 40 g of isopropylamine in 40 ml of ethanol is heated to boiling for 4 hours. Thereafter the mixture is concentrated by evaporation in vacuo and the residue is dissolved in 2 N hydrochloric acid. After extraction with ether, the hydrochloric acid layer is separated off and rendered alkaline by adding concentrated sodium hydroxide solution. The base which has separated out is extracted by shaking with methylene chloride. After evaporation of the solvent and after recrystallisation of the residue from ethyl acetate, the 1-[o-chloro-p-(N',N'-dimethylureido)-phenoxy]-2-hydroxy-3-isopropylamino-propane of formula ##STR18## is obtained in crystals of melting point 130° C.

Workup

  1. concentrationThereafter the mixture is concentrated by evaporation in vacuo
  2. dissolutionthe residue is dissolved in 2 N hydrochloric acid
  3. extractionAfter extraction with ether
  4. customthe hydrochloric acid layer is separated off
  5. additionby adding concentrated sodium hydroxide solution
  6. customThe base which has separated out
  7. extractionis extracted
  8. customAfter evaporation of the solvent
  9. customafter recrystallisation of the residue from ethyl acetate

Sources & evidence

ORD record
ord-91ed93f5de1b4419857cdfdea9474792
Source dataset
uspto-grants-1978_10
Patent number
US04120978

Reaction notes

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