1,4-Benzenedimethanol → HCID 86762464, compound

HRID 1028861Notes

Reaction equation

HRID 1028861 reaction equation
[N:1]([C:4]1[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1)=[C:2]=[O:3].[C:14]1([CH2:22][OH:23])[CH:19]=[CH:18][C:17]([CH2:20][OH:21])=[CH:16][CH:15]=1>CN(C=O)C.CN(C1C=CN=CC=1)C>[C:4]1([NH:1][C:2](=[O:3])[O:21][CH2:20][C:17]2[CH:18]=[CH:19][C:14]([CH2:22][OH:23])=[CH:15][CH:16]=2)[C:13]2[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=2)[CH:7]=[CH:6][CH:5]=1

Participants

5

Reactant 2

HCID 115061,4-BenzenedimethanolHCID 66589alpha-Naphthyl isocyanate

Product 1

HCID 86762464HCID 86762464, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6228DimethylformamideSolvent

Procedure

To a solution of 1-isocyanatonaphthalene (1.69 g, 10 mmol) and 1,4-phenylene-dimethanol (4.14 g, 30 mmol) in anhydrous DMF was added DMAP (0.06 g, 0.5 mmol). The resulting mixture was stirred at room temperature for 12 h. The solvent was removed in vacuo to give a solid, which was recrystallized using ethyl acetate to produce 7 (1.72 g, 5.6 mmol) as a white solid in 56% yield: m.p.: 158-159° C.; IR (thin film): 3325, 1691, 1542, 1420, 1245, 1237 cm−1; 1H NMR (500 MHz, CDCl3): 6 1H NMR (500 MHz, CDCl3) δ 7.95-7.83 (m, 3H), 7.68 (d, J=8.2 Hz, 1H), 7.58-7.47 (m, 4H), 7.44-7.35 (m, 3H), 5.27 (s, 2H), 4.73 (d, J=5.8 Hz, 2H), 1.70 (t, J=6.0 Hz, 1H) ppm; 13C NMR (75 MHz, CDCl3): δ 154.43, 141.33, 140.53, 136.51, 135.70, 134.28, 132.55, 128.98, 128.90, 127.44, 127.41, 126.49, 126.24, 126.02, 125.35, 120.61, 67.25, 65.24 ppm. HRMS (m/z): [M+Na]+ calcd. for C19H17NNaO3, 330.1100; found, 330.1095.

Workup

  1. customThe solvent was removed in vacuo
  2. customto give a solid, which
  3. customwas recrystallized

Sources & evidence

ORD record
ord-5d256b58e91344e5bf2bec9838fa729f
Source dataset
uspto-grants-2014_05
Patent number
US08735622B2

Reaction notes

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