Chlorosuccinimide → HCID 11176970, compound

HRID 895244Notes

Reaction equation

HRID 895244 reaction equation
[Br:1][C:2]1[C:3]([OH:21])=[CH:4][C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=1)=[CH:7][C:6]=2[Cl:20].C1C(=O)N([Cl:29])C(=O)C1>C1COCC1>[Br:1][C:2]1[C:3]([OH:21])=[C:4]([Cl:29])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([C:12]1[CH:13]=[CH:14][C:15]([O:18][CH3:19])=[CH:16][CH:17]=1)=[CH:7][C:6]=2[Cl:20]

Participants

4

Reactant 2

HCID 31398ChlorosuccinimideHCID 11210712HCID 11210712, compound

Product 1

HCID 11176970HCID 11176970, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The title compound was prepared by reacting 3-bromo-8-chloro-6-(4-methoxyphenyl)-2-naphthol (0.69 g, 1.90 mmol) and NCS (0.31 g, 2.3 mmol) in THF (25 mL) according to method C to yield 0.61 g (81%) of a yellow solid. An analytical sample was further prepared by reverse phase preparative HPLC to yield the title compound as a white solid: mp 176-178° C. (dec.); 1H NMR (DMSO-d6): δ 3.82 (3H, s), 7.08 (2H, d, J=8.77 Hz), 7.77 (2H, d, J=8.75 Hz), 8.00 (1H, d, J=1.84 Hz), 8.19 (1H, d, J=1.84 Hz), 8.39 (1H, s), 10.53 (1H, bs); MS (ESI) m/z39513971399 (M−H)−.

Sources & evidence

ORD record
ord-eaecca17d4f94fd697f9f1389db9c624
Source dataset
uspto-grants-2005_07
Patent number
US06914074B2

Reaction notes

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