Sulfuric Acid → HCID 13562947, compound

HRID 2118517Notes

Reaction equation

HRID 2118517 reaction equation
[CH:1]([N:3]([CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=1)[CH2:4][C:5]1[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=1[Cl:11])=O.P(Cl)(Cl)(Cl)=O.[S:29](=[O:33])(=[O:32])([OH:31])[OH:30]>C1(C)C=CC=CC=1.C(O)(C)C>[S:29]([O-:33])([OH:32])(=[O:31])=[O:30].[Cl:11][C:6]1[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=1[CH2:4][N+:3]1[CH2:12][CH2:13][C:14]2[C:19](=[CH:18][C:17]([O:20][CH3:21])=[C:16]([O:22][CH3:23])[CH:15]=2)[CH:1]=1

Participants

6

Reactant 3

HCID 1118Sulfuric AcidHCID 24813Phosphorus oxychlorideHCID 20194016HCID 20194016, compound

Product 1

HCID 13562947HCID 13562947, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 3776IsopropanolSolvent

Procedure

N-Formyl-N(2-chlorobenzyl)-2(3,4-dimethoxyphenyl)-ethylamine (12.1 g) are dissolved in toluene (50 ml), combined with phosphorus oxychloride (15.2 g=9 ml) and heated under reflux for 1.5 hours. The mixture is concentrated, the residue is mixed with ice, made alkaline with potassium carbonate and extracted with ethyl acetate. The ethyl acetate extract is concentrated by evaporation. The residue obtained is dissolved in isopropanol and mixed with conc. sulphuric acid (2 ml). After cooling, the mixture is suction filtered, washed with isopropanol and ether and dried. Yield: 8.6 g. Melting point: 226°-228° C.

Workup

  1. temperatureheated
  2. temperatureunder reflux for 1.5 hours
  3. concentrationThe mixture is concentrated
  4. additionthe residue is mixed with ice
  5. extractionextracted with ethyl acetate
  6. extractionThe ethyl acetate extract
  7. concentrationis concentrated by evaporation
  8. customThe residue obtained
  9. temperatureAfter cooling
  10. filtrationfiltered
  11. washwashed with isopropanol and ether
  12. customdried

Sources & evidence

ORD record
ord-2adbd7b591bd4e62ba1076c0d2578fd1
Source dataset
uspto-grants-1987_07
Patent number
US04678792

Reaction notes

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