Triethylamine → HCID 23497814, compound

HRID 2076442Notes

Reaction equation

HRID 2076442 reaction equation
[CH3:1][C:2]1([CH3:17])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]2[CH:7]=[C:6]([C:14](O)=[O:15])[CH:5]=[CH:4][C:3]1=2.[I:18][C:19]1[CH:24]=[CH:23][C:22]([NH2:25])=[CH:21][CH:20]=1.CCN(CC)CC.[NH4+].[Cl-]>O=S(Cl)Cl.CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)Cl>[I:18][C:19]1[CH:24]=[CH:23][C:22]([NH:25][C:14]([C:6]2[CH:5]=[CH:4][C:3]3[C:2]([CH3:17])([CH3:1])[CH2:11][CH2:10][C:9]([CH3:13])([CH3:12])[C:8]=3[CH:7]=2)=[O:15])=[CH:21][CH:20]=1

Participants

9

Reactant 4

HCID 8471TriethylamineHCID 108934-IodoanilineHCID 25517Ammonium ChlorideHCID 2276385,5,8,8-Tetramethyl-5,6,7,8-tetrahydronaphthalene-2-carboxylic acid

Product 1

HCID 23497814HCID 23497814, compoundYield 56%

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
0 °C

Procedure

5,5,8,8-Tetramethyl-5,6,7,8-tetrahydro-naphthalene-2-carboxylic acid 2 (1.38 g, 5.94 mmol) was dissolved in SOCl2 and two drops of DMF were added at 0° C. The mixture was stirred at 0° C. for 30 min and it was evaporated and this crude product was dissolved in CH2Cl2 (5 mL). B) 4-iodophenylamine (1.30 g, 5.94 mmol) and DMAP (73 mg, 0.59 mmol) were dissolved in CH2Cl2 (10 mL) and Et3N (8.4 mL) was added at 0° C. The Mixture A) was added in B) at 0° C. via syringe and the resulting mixture was stirred at 0° C. for 10 min and abandoned at RT for 2.5 h. A solution of aqueous NH4Cl 5% (50 mL) was added and the resulting mixture was extracted with EtOAc (3×150 mL). The organic layer was washed with NaHCO3 (2×100 mL) and brine (3×100 mL) and dried with MgSO4, filtered and evaporated. The crude product was purified by column chromatography using as eluent cyclohexane:EtOAc=90:10. 5,6,7,8-Tetrahydro-N-(4-iodophenyl)-5,5,8,8-tetramethylnaphthalene-2-carboxamide 22 was obtained (1.43 g, 56% yield) as a white solid.

Workup

  1. customit was evaporated
  2. dissolutionthis crude product was dissolved in CH2Cl2 (5 mL)
  3. additionThe Mixture A) was added in B) at 0° C. via syringe
  4. stirringthe resulting mixture was stirred at 0° C. for 10 min
  5. waitabandoned at RT for 2.5 h
  6. extractionthe resulting mixture was extracted with EtOAc (3×150 mL)
  7. washThe organic layer was washed with NaHCO3 (2×100 mL) and brine (3×100 mL)
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. customevaporated
  11. customThe crude product was purified by column chromatography

Sources & evidence

ORD record
ord-2e22fca88f5b4bebaea72d6a4e04a9b5
Source dataset
uspto-grants-2011_04
Patent number
US07923579B2

Reaction notes

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