Dimethylformamide → HCID 22337835, compound

HRID 585599Notes

Reaction equation

HRID 585599 reaction equation
C[C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13]Cl.[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:22]([OH:26])=[CH:21][CH:20]=[CH:19][C:18]=2[CH:17]=1.[H-].[Na+].[CH3:29]N(C)C=O>>[NH2:15][C:16]1[CH:25]=[CH:24][C:23]2[C:18](=[CH:19][CH:20]=[CH:21][C:22]=2[O:26][CH:13]([CH3:29])[C:3]2[N:4]=[C:5]([C:7]3[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=3)[O:6][CH:2]=2)[CH:17]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 902956-AminonaphtholHCID 97942894-(Chloromethyl)-5-methyl-2-phenyl-1,3-oxazole

Product 1

HCID 22337835HCID 22337835, compoundYield 30%

Procedure

5-methyl-2-phenyl-4-Chloromethyloxazole (3.34 g) is added to a chilled mixture of 2-Amino-5-naphthol (2.55 g) and sodium hydride (0.65 g) in dimethylformamide (100 mL). Let stir overnight at room temperature. Concentrate in vacuo. Redilute with ethylacetate and absorb onto silica gel. Chromatograph (ethyl acetate/hexane) to give 2-amino-5-(methyl-2-phenyl-oxazol-4-ylmethoxy)naphthalene (1.59 g, 30%). Without further characterization this amine and triethylamine (0.67 mL) were dissolved in dichloromethane (75 mL). Cooled in an acetone and dry ice bath. Triflic anhydride (0.81 mL) was added and the mixture had warmed to room temperature overnight. Partition between water and ethyl acetate. Separate and dry with magnesium sulfate. Concentrate at rotovap, and triturate with ethyl acetate to provide the title compound (0.70 g, 30%) as a white solid, m.p. 192-194° C. 1H NMR (DMSO-d6, 400 MHz): δ 2.49 (s, 3H), 5.21 (s, 2H), 7.17 (d, 1H), 7.36 (d, 1H), 7.46-755 (m, 5H), 7.73 (s, 1H), 7.93-7.97 (m, 2H), 8.13 (d, 1H). MS [EI, m/z]: 462 [M]+. Anal. Calcd. for C22H17F3N2O4S 0.75(H2O): C, 55.52; H, 3.92; N, 5.89. Found: C, 55.62; H, 4.13; N, 5.45.

Workup

  1. concentrationConcentrate in vacuo
  2. additionRedilute with ethylacetate
  3. customabsorb onto silica gel

Sources & evidence

ORD record
ord-233a1ef688d34c35b56e9d34235f1977
Source dataset
uspto-grants-2005_08
Patent number
US06933322B2

Reaction notes

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