Triethylamine → HCID 21962617, compound

HRID 2211937Notes

Reaction equation

HRID 2211937 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][C:15]2[O:19][C:18]([C:20](Cl)=[O:21])=[CH:17][CH:16]=2)=[CH:4][C:5]2[C:6]([CH3:13])([CH3:12])[CH2:7][CH2:8][CH2:9][C:10]=2[CH:11]=1.Cl.[CH3:24][O:25][C:26]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[C:27]=1[NH2:28].C(N(CC)CC)C>C(OCC)(=O)C>[O:25]([C:26]1[CH:32]=[C:31]([O:33][CH3:34])[CH:30]=[C:29]([O:35][CH3:36])[C:27]=1[NH:28][C:20]([C:18]1[O:19][C:15]([CH2:14][C:3]2[C:2]([CH3:1])=[CH:11][C:10]3[CH2:9][CH2:8][CH2:7][C:6]([CH3:13])([CH3:12])[C:5]=3[CH:4]=2)=[CH:16][CH:17]=1)=[O:21])[CH3:24]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 27644342,4,6-trimethoxyaniline HydrochlorideHCID 21962621HCID 21962621, compound

Product 1

HCID 21962617HCID 21962617, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 5-[(3,8,8-trimethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furoyl chloride (10 eq, 0.32 mmol, 0.2M) in 2 mL ethyl acetate, the 2,4,6 trimethoxy aniline mono HCl salt (10 eq, 0.32 mmol) was added. Triethyl amine (excess) was added to this mixture and stirred overnight. The crude product was dried under vacuo and purified through plug column chromatography (1:100 crude mass/silicagel ratio) by eluting with 20 and 30 percent ethyl acetate/hexane solution. In some cases, the regio-isomers were separated by recrystallization in twenty five percent ethyl acetate/hexanes (1 g/75 mL compound/volume) to yield N-(2,4,6-trimethoxylphenyl)-5-[(3,8,8-trimethyl-5,6,7,8-tetrahydro-2-naphthalenyl)methyl]-2-furamide (120 mgs, 82% yield). 1H NMR (CDCl3) 7.28 ppm (1H, broad), 7.12 (1H, s), 7.08 (1H, 3=3.40 Hz, d), 6.89 (1H, s), 6.19 (2H, s), 6.00 (1H, J=3.40 Hz, d), 3.97 (2H, s), 3.83 (3H, s), 3.82 (6H, s) 2.73 (2H, J=6.05 Hz, t), 2.25 (3H, s), 1.84-1.76(2H, multiplet), 1.69-1.63 (2H, multiplet), 1.59 (3H, s), 1.26(6H, s) elemental: expected C(72.55), H(7.18), N(3.02); actual C(72.67), H(7.22), N(2.98).

Workup

  1. dry with materialThe crude product was dried under vacuo
  2. custompurified through plug column chromatography (1:100 crude mass/silicagel ratio)
  3. washby eluting with 20 and 30 percent ethyl acetate/hexane solution
  4. customIn some cases, the regio-isomers were separated by recrystallization in twenty five percent ethyl acetate/hexanes (1 g/75 mL compound/volume)

Sources & evidence

ORD record
ord-aabdff1269cf4aaa8aa0fed794a25a6a
Source dataset
uspto-grants-2006_09
Patent number
US07101878B1

Reaction notes

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