Benzene → HCID 67859241, compound

HRID 1646169Notes

Reaction equation

HRID 1646169 reaction equation
C1C=CC=CC=1.[C:7](Cl)(=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[CH2:16]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH2:30]C)[C:25](=[C:32]([S:35][CH2:36][CH:37]([OH:45])[CH2:38][N:39]1[CH2:44][CH2:43][O:42][CH2:41][CH2:40]1)[C:33]#[N:34])[NH:24][CH2:23][CH2:22]2)C>C(N(CC)CC)C>[CH3:16][O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH3:30])[C:25](=[C:32]([S:35][CH2:36][CH:37]([O:45][C:7](=[O:14])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)[CH2:38][N:39]1[CH2:40][CH2:41][O:42][CH2:43][CH2:44]1)[C:33]#[N:34])[NH:24][CH2:23][CH2:22]2

Participants

5

Reactant 3

HCID 241BenzeneHCID 7412Benzoyl chlorideHCID 67859005HCID 67859005, compound

Product 1

HCID 67859241HCID 67859241, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

After adding 40 ml of benzene, 1.0 g of triethylamine and 1.5 g of benzoyl chloride to 4.06 g of 2-(6,7-diethoxy-1,2,3,4-tetrahydro-1-isoquinolinylidene)-2-[2-hydroxy-3-(4-morpholinyl)propyl]mercaptoacetonitrile, the reaction mixture is refluxed for 45 minutes, then cooled down and filtered. After evaporating the filtrate, the residue crystallizes out on adding ethyl acetate to obtain the named product in a yield of 3.25 g, m.p.: 144° C. (from isopropanol).

Workup

  1. temperaturethe reaction mixture is refluxed for 45 minutes
  2. temperaturecooled down
  3. filtrationfiltered
  4. customAfter evaporating the filtrate
  5. customthe residue crystallizes out
  6. additionon adding ethyl acetate
  7. customto obtain the named product in a yield of 3.25 g, m.p.: 144° C. (from isopropanol)

Sources & evidence

ORD record
ord-c54dd95bf93e47ae85c436c59206e68b
Source dataset
uspto-grants-1993_01
Patent number
US05179089

Reaction notes

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