Benzene → HCID 67858919, compound

HRID 1646170Notes

Reaction equation

HRID 1646170 reaction equation
C1C=CC=CC=1.[C:7]([Cl:15])(=[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][CH3:31])[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)[CH3:17]>C(N(CC)CC)C>[ClH:15].[CH2:16]([O:18][C:19]1[CH:20]=[C:21]2[C:26](=[CH:27][C:28]=1[O:29][CH2:30][CH3:31])[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)[CH3:17]

Participants

5

Reactant 3

HCID 241BenzeneHCID 7412Benzoyl chlorideHCID 67859005HCID 67859005, compound

Product 1

HCID 67858919HCID 67858919, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

40 ml of benzene, 1.0 g of triethylamine and 1.5 g of benzoyl chloride are added to 4.34 g of 2-(6,7-diethoxy-1,2,3,4-tetrahydro-1-isoquinolinylidene)-2-[2-hydroxy-3-(4-morpholinyl)propyl]mercaptoacetonitrile and the reaction mixture is refluxed for 45 minutes, then cooled down. After filtering and evaporating the solvent under reduced pressure, the residue is dissolved in isopropanol and acidified by adding abs. ethanolic hydrogen chloride solution. In this way 3.77 g of the named hydrochloride crystallize out, m.p.: 207° C. (from ethanol).

Workup

  1. temperaturethe reaction mixture is refluxed for 45 minutes
  2. temperaturecooled down
  3. filtrationAfter filtering
  4. customevaporating the solvent under reduced pressure
  5. dissolutionthe residue is dissolved in isopropanol
  6. additionby adding abs
  7. customIn this way 3.77 g of the named hydrochloride crystallize out

Sources & evidence

ORD record
ord-eabc915fcf874d8cad30650f697a4bd7
Source dataset
uspto-grants-1993_01
Patent number
US05179089

Reaction notes

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