Chlorosuccinimide → HCID 10125582, compound

HRID 1830651Notes

Reaction equation

HRID 1830651 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([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)[CH:5]=[CH:6][C:7]=1[OH:8].C1C(=O)N([Cl:27])C(=O)C1>C1COCC1>[Cl:27][C:15]1[C:16]2[C:11](=[CH:10][C:9]([C:4]3[CH:5]=[CH:6][C:7]([OH:8])=[C:2]([Cl:1])[CH:3]=3)=[CH:18][CH:17]=2)[CH:12]=[CH:13][C:14]=1[OH:19]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 102860876-(3-Chloro-4-hydroxyphenyl)-2-naphthalenol

Product 1

HCID 10125582HCID 10125582, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 6-(3-chloro-4-hydroxyphenyl)-2-naphthol (500 mg, 1.85 mmol) and NCS (346 mg, 2.59 mmol) in THF (37 mL) according to method A to yield 380 mg (68%) of yellowish solid: mp 174–175° C.; 1H NMR (DMDO-d6): δ 7.09 (1H, d, 8.47 Hz), 7.31 (1H, d, J=8.89 Hz), 7.60 (1H, dd, J=8.20 Hz, J=2.26 Hz), 7.78 (1H, d, J=2.22 Hz), 7.84 (1H, d, J=8.99 Hz), 7.88 (1H, dd, J=9.00 Hz, J=1.80 Hz), 8.05 (1H, d, J=8.86 Hz), 8.14 (1H, d, J=1.60 Hz), 10.37 (1H, s), 10.49 (1H, s); MS (ESI) m/z 303/305/307 (M−H)−.

Sources & evidence

ORD record
ord-0842e8f5094b4729b13b1bdbb9189724
Source dataset
uspto-grants-2006_06
Patent number
US07067524B2

Reaction notes

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