Benzoyl chloride → N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamide

HRID 653808Notes

Reaction equation

HRID 653808 reaction equation
[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH2:14])[CH:5]=[CH:4][C:3]1=2.[C:16](Cl)(=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>N1C=CC=CC=1.O1CCCC1>[CH3:1][C:2]1([CH3:15])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([NH:14][C:16](=[O:23])[C:17]3[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=3)[CH:5]=[CH:4][C:3]1=2

Participants

5

Reactant 2

HCID 7412Benzoyl chlorideHCID 114697605,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalen-2-amine

Product 1

HCID 9839567N-(5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthyl)benzamideYield 80.7%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8028TetrahydrofuranSolvent

Procedure

2.5 g of 5,6,7,8-tetrahydro-5,5,8,8-tetramethyl-2-naphthylamine were dissolved in 50 ml of pyridine and treated at room temperature with a solution of 1.7 g of benzoyl chloride in 20 ml of tetrahydrofuran. After stirring at room temperature for two hours the reaction mixture was poured on to ice-water and, after acidification with 3N hydrochloric acid, extracted with ethyl acetate. The oil obtained after drying and evaporating the organic phase was crystallized from hexane/ethyl acetate and gave 3 g of N-(5,6,7,8-tetrahydro-5,5,8.8-tetramethyl-2-naphthyl)benzamide in white crystals, m.p. 146° C.-148° C.

Workup

  1. extractionafter acidification with 3N hydrochloric acid, extracted with ethyl acetate
  2. customThe oil obtained
  3. customafter drying
  4. customevaporating the organic phase
  5. customwas crystallized from hexane/ethyl acetate

Sources & evidence

ORD record
ord-77cf3f993fc844c08a244527c4955f82
Source dataset
uspto-grants-1992_07
Patent number
US05128470

Reaction notes

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