Thionyl Chloride → 3,5-Dimethoxy-2-methyl-N-(3-chloro-tricyclo[3.3.1.13,7]dec-1ylmethyl)-benzamide

HRID 1532335Notes

Reaction equation

HRID 1532335 reaction equation
[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([OH:8])=O.S(Cl)([Cl:17])=O.[C:19]12([CH2:29][NH2:30])[CH2:28][CH:23]3[CH2:24][CH:25]([CH2:27][CH:21]([CH2:22]3)[CH2:20]1)[CH2:26]2>ClCCl.C(N(CC)CC)C>[CH3:1][O:2][C:3]1[C:4]([CH3:14])=[C:5]([CH:9]=[C:10]([O:12][CH3:13])[CH:11]=1)[C:6]([NH:30][CH2:29][C:19]12[CH2:26][CH:25]3[CH2:24][CH:23]([CH2:22][C:21]([Cl:17])([CH2:27]3)[CH2:20]1)[CH2:28]2)=[O:8]

Participants

6

Reactant 3

HCID 24386Thionyl ChlorideHCID 86625Tricyclo(3.3.1.13,7)dec-1-ylmethylamineHCID 183655283,5-Dimethoxy-2-methylbenzoic acid

Product 1

HCID 206700603,5-Dimethoxy-2-methyl-N-(3-chloro-tricyclo[3.3.1.13,7]dec-1ylmethyl)-benzamide

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8471TriethylamineSolvent

Procedure

A mixture of 3,5-dimethoxy-2-methylbenzoic acid from Example 67 a) (0.15 g) and thionyl chloride (2 ml) was heated to reflux temperature for 2 minutes before cooling to room temperature and concentratedunder reduced pressure. The residue was dissolved in dichloromethane (1 ml) and added to a solution of 1-adamantanemethylamine (0.104 g) in dichloromethane (5 ml) and triethylamine (1 ml) and the resulting reaction mixture stirred for 2 days. The reaction was partitioned between dichloromethane (100 ml) and aqueous hydrochloric acid (0.5M, 50 ml). The organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate (50 ml), dried over anhydrous magnesium sulphate, filtered and concentrated under reduced pressure. The residue was purified by HPLC over a Dynamax® column eluting with iso-hexane: ethyl acetate (4:1) to give the title compound as a colourless solid (0.090 g).

Workup

  1. temperaturewas heated
  2. temperatureto reflux temperature for 2 minutes
  3. customthe resulting reaction mixture
  4. customThe reaction was partitioned between dichloromethane (100 ml) and aqueous hydrochloric acid (0.5M, 50 ml)
  5. washThe organic phase was washed with a saturated aqueous solution of sodium hydrogen carbonate (50 ml)
  6. dry with materialdried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by HPLC over a Dynamax® column
  10. washeluting with iso-hexane: ethyl acetate (4:1)

Sources & evidence

ORD record
ord-2e6ff848bcc8418bb9482d0c285d5a1c
Source dataset
uspto-grants-2001_03
Patent number
US06201024B1

Reaction notes

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