Chlorosuccinimide → HCID 10308458, compound

HRID 895204Notes

Reaction equation

HRID 895204 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([OH:8])[CH:5]=[CH:4][C:3]=1[C:9]1[CH:10]=[C:11]2[C:16](=[CH:17][CH:18]=1)[CH:15]=[C:14]([OH:19])[CH:13]=[CH:12]2.C1C(=O)N([Cl:27])C(=O)C1>C1COCC1>[Cl:27][C:15]1[C:16]2[C:11](=[CH:10][C:9]([C:3]3[CH:4]=[CH:5][C:6]([OH:8])=[CH:7][C:2]=3[Cl:1])=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[OH:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 10308197HCID 10308197, compound

Product 1

HCID 10308458HCID 10308458, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-(2-chloro-4-hydroxyphenyl)-2-naphthol (500 mg, 1.85 mmol) and NCS (321 mg, 2.40 mmol) in THF (40 mL) according to method C to yield 435 mg (77%) of yellowish solid: mp 224-226° C.; 1H NMR (DMDO-d6): δ 6.86 (1H, dd, J=8.42 Hz, J=2.41 Hz), 6.96 (1H, d, J=2.44 Hz), 7.30 (1H, d, J=3.19 Hz), 7.33 (1H, d, J=2.65 Hz), 7.62 (1H, dd, J=8.81 Hz, J=1.71 Hz), 7.83 (1H, d, J=8.93 Hz), 7.86 (1H, d, J=1.54 Hz), 8.04 (1H, J=8.76 Hz), 10.04 (1H, s), 10.51 (1H, s); 13C NMR (DMDO-d6): δ 112.24, 114.84, 116.26, 118.79, 121.84, 128.16, 128.24, 128.35, 129.27, 130.03, 130.40, 131.73, 132.38, 133.98, 151.24, 157.70; MS (ESI) m/z 303/305/307 (M−H)−.

Sources & evidence

ORD record
ord-763e03d113c64228afa2329cbfef1fe6
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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