Benzoyl chloride → 8-Chloro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthalene

HRID 1975770

Reaction equation

HRID 1975770 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([NH:12]CCC)[CH2:8][CH2:7]2.C(N([CH2:21][CH3:22])CC)C.[C:23](Cl)(=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1.[C:32](=O)([O-])[O-].[Na+].[Na+]>ClCCl>[Cl:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:11]=1[CH2:10][CH:9]([NH:12][C:23](=[O:30])[C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][C:25]=1[CH2:32][CH2:21][CH3:22])[CH2:8][CH2:7]2

Participants

6

Reactant 4

HCID 7412Benzoyl chlorideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 149692298-chloro-2-(N-n-propylamino)tetralin

Product 1

HCID 190326628-Chloro-2-(n-propylbenzoyl)amino-1,2,3,4-tetrahydronaphthaleneYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 53 g (0.23 mol) 8-chloro-2-(n-propyl)amino-1,2,3,4-tetrahydronaphthalene and 50 ml triethylamine in 500 ml dichloromethane was added dropwise 33 ml (40 g, 0.28 mol) benzoylchloride. After stirring over night at room temperature, 10% sodium carbonate was added and the mixture was shaken and separated. The organic phase was dried (magnesium sulphate), filtered and evaporated yielding 72 g (95%) raw product.

Workup

  1. stirringthe mixture was shaken
  2. customseparated
  3. dry with materialThe organic phase was dried (magnesium sulphate)
  4. filtrationfiltered
  5. customevaporated

Sources & evidence

ORD record
ord-5085cde565dd4687b94d649c15c06601
Source dataset
uspto-grants-1994_02
Patent number
US05288748

Linked notes

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