N,N-Diethylaniline → Trioxsalen

HRID 225031Notes

Reaction equation

HRID 225031 reaction equation
[CH3:1][C:2]1[C:11]2[C:6](=[C:7]([CH3:17])[C:8]([O:12][CH2:13][C:14](Cl)=C)=[CH:9][CH:10]=2)[O:5][C:4](=[O:18])[CH:3]=1.[CH2:19](N(CC)C1C=CC=CC=1)C>CCOCC>[CH3:1][C:2]1[C:11]2[CH:10]=[C:9]3[C:8](=[C:7]([CH3:17])[C:6]=2[O:5][C:4](=[O:18])[CH:3]=1)[O:12][C:13]([CH3:14])=[CH:19]3

Participants

4

Reactant 2

HCID 7061N,N-DiethylanilineHCID 132080597-[(2-Chloroprop-2-en-1-yl)oxy]-4,8-dimethyl-2H-1-benzopyran-2-one

Product 1

HCID 5585TrioxsalenYield 41.6%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 4,8-dimethyl-7-(2'-chloroallyloxy)coumarin (500 mg., 1.89 m mole) and N,N-diethylaniline (5.0 ml) was protected by an "Aquasorb" (TM), brand of phosphorous pentoxide drying tube, while being heated under reflux for twenty-four hours at an oil bath temperature of 220°-225° C. Treatment of the reaction mixture as described in part 1-B gave some black, ether-insoluble material which was discarded. The desired 4,5',8-trimethylpsoralene was obtained as a tan solid (154 mg., 41.6% yield), which was recrystallized from 95% ethanol to obtain light tan needles (53 mg., 14% yield) of m.p. 233° C. (rptd: m.p. 234° C.). Its infrared spectrum was identical to that of a commercial sample.

Workup

  1. customwas protected by an "Aquasorb" (TM), brand of phosphorous pentoxide drying tube
  2. temperaturewhile being heated
  3. temperatureunder reflux for twenty-four hours at an oil bath temperature of 220°-225° C

Sources & evidence

ORD record
ord-f2f04d8fcc324ecbbb91fcc1267ecb3e
Source dataset
uspto-grants-1980_11
Patent number
US04235781

Reaction notes

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