Dabco → HCID 44550981, compound

HRID 2238403Notes

Reaction equation

HRID 2238403 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2.C1N2CCN(CC2)C1.[CH3:24][N:25]([CH3:29])[C:26](Cl)=[S:27]>CN(C=O)C>[CH3:24][N:25]([CH3:29])[C:26]([O:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[CH:8]=[C:7]([C:12]([O:14][CH3:15])=[O:13])[CH:6]=[CH:5]2)=[S:27]

Participants

5

Reactant 3

HCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 390995Methyl 6-hydroxy-2-naphthoate

Product 1

HCID 44550981HCID 44550981, compoundYield 88%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A mixture of methyl 6-hydroxy-2-naphthoate [J. Med. Chem., 2001, 44, 2869-2878] (156) (5.95 g, 29.4 mmol), DABCO (6.61 g, 58.9 mmol) and dimethylthiocarbamoyl chloride (5.46 g, 44.2 mmol) in dry DMF (40 mL) was stirred at room temperature for 8 h. The precipitated solid was collected, washed with water and dissolved in CH2Cl2. The solution was filtered through a column of silica gel and the product was triturated with i-Pr2O and recrystallised from CH2Cl2/hexane to give methyl 6-{[(dimethylamino)carbothioyl]oxy}-2-naphthoate (157) (7.47 g, 88%) as a white solid: mp 144-147° C.; 1H NMR [(CD3)2SO] δ 8.66 (s, 1H), 8.16 (d, J=9.0 Hz, 1H), 8.03 (d, J=8.7 Hz, 1H), 8.00 (dd, J=−8.6, 1.5 Hz, 1H), 7.70 (d, J=−2.3 Hz, 1H), 7.389 (dd, J=8.9, 2.3 Hz, 1H), 3.93 (s, 3H), 3.40 (s, 3H), 3.38 (s, 3H). Anal. (C15H15NO3S) C, H, N.

Workup

  1. customThe precipitated solid was collected
  2. washwashed with water
  3. dissolutiondissolved in CH2Cl2
  4. filtrationThe solution was filtered through a column of silica gel
  5. customthe product was triturated with i-Pr2O
  6. customrecrystallised from CH2Cl2/hexane

Sources & evidence

ORD record
ord-7dae9b5fdb654d61b19d3e7f63e0743f
Source dataset
uspto-grants-2010_05
Patent number
US07718688B2

Reaction notes

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