Water → 3-(Phenyliminomethyl)dibenzo[b,f]thiepin-5,5-dioxide

HRID 485110Notes

Reaction equation

HRID 485110 reaction equation
[CH:1]1[C:11]2[CH:10]=[CH:9][C:8]3[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=3[S:6](=[O:17])(=[O:16])[C:5]=2[CH:4]=[C:3]([CH:18]=O)[CH:2]=1.[NH2:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1.O>C1(C)C=CC=CC=1>[C:21]1([N:20]=[CH:18][C:3]2[CH:2]=[CH:1][C:11]3[CH:10]=[CH:9][C:8]4[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=4[S:6](=[O:17])(=[O:16])[C:5]=3[CH:4]=2)[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6115AnilineHCID 13520245Dibenzo[b,f]thiepin-3-carboxaldehyde 5,5-dioxide

Product 1

HCID 202715043-(Phenyliminomethyl)dibenzo[b,f]thiepin-5,5-dioxide

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Heat a mixture of 675 mg (2.5 mmoles) of dibenzo[b,f]thiepin-3-carboxaldehyde-5,5-dioxide and 465 mg of aniline (5 mmoles) in 20 ml of toluene, under reflux, with azetropic removal of water for 21 hours. Cool the mixture and filter the insoluble product. Stir the solid in 10 ml of ether containing a few drops of THF for 10 minutes then filter to obtain the pure product, 704 mg, mp: 184°-185°.

Workup

  1. temperatureHeat
  2. temperatureCool the mixture
  3. filtrationfilter the insoluble product
  4. filtrationthen filter
  5. customto obtain the pure product, 704 mg, mp: 184°-185°

Sources & evidence

ORD record
ord-54cc05676c3b4bd795500ef9ec0ae011
Source dataset
uspto-grants-1985_08
Patent number
US04535171

Reaction notes

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