Chlorosuccinimide → HCID 11483402, compound

HRID 895197Notes

Reaction equation

HRID 895197 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6]([C:9]2[CH:10]=[C:11]3[C:16](=[CH:17][CH:18]=2)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]3)=[C:5]([CH3:20])[CH:4]=1.C1C(=O)N([Cl:28])C(=O)C1>C1COCC1>[Cl:28][C:15]1[C:16]2[C:11](=[CH:10][C:9]([C:6]3[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][C:5]=3[CH3:20])=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[OH:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11459740HCID 11459740, compound

Product 1

HCID 11483402HCID 11483402, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-(4-methoxy-2-methylphenyl)-2-naphthol (800 mg, 3.03 mmol) and NCS (485 mg, 3.61 mmol) in THF (30 mL) according to method A to yield 640 mg (71%) of yellow solid: 1H NMR (DMDO-d6): δ 2.26 (3H, s), 3.79 (3H, s), 6.86 (1H, dd, J=8.36 Hz, J=2.63 Hz), 6.91 (1H, d, J=2.51 Hz), 7.22 (1H, d, J=8.34 Hz), 7.31 (1H, d, J=8.89 Hz), 7.56 (1H, dd, J=8.71 Hz, J=1.71 Hz), 7.79-7.83(2H, m), 8.04 (1H, J=8.91 Hz), 10.46 (1H, s); 13C NMR (DMDO-d6): δ 20.54, 55.07, 111.48, 112.21, 115.71, 118.73, 121.94, 127.92, 128.15, 128.35, 129.34, 130.12. 130.87, 133.26, 136.14, 136.36, 150.99, 158.49; MS (ESI) m/z297/299 (M−H)−.

Sources & evidence

ORD record
ord-ed6610b0f83749188641fbcbe36dd8bd
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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