Ethanol → 4-(3-{[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-3H-thiazol-2-one

HRID 1161100Notes

Reaction equation

HRID 1161100 reaction equation
[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:27])[C:17]3[CH:18]=[C:19]([C:23](=O)[CH2:24]Cl)[CH:20]=[CH:21][CH:22]=3)=[CH:12][CH:11]=2)=[C:6]([Cl:30])[C:5]=1[OH:31])(=[O:3])[CH3:2].[S-:32][C:33]#[N:34].[K+].C([OH:38])C>>[C:1]([C:4]1[CH:29]=[CH:28][C:7]([O:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([CH:16]([OH:27])[C:17]3[CH:18]=[C:19]([C:23]4[NH:34][C:33](=[O:38])[S:32][CH:24]=4)[CH:20]=[CH:21][CH:22]=3)=[CH:12][CH:11]=2)=[C:6]([Cl:30])[C:5]=1[OH:31])(=[O:3])[CH3:2]

Participants

4

Reactant 3

HCID 702EthanolHCID 516872Potassium thiocyanateHCID 866205991-(3-{[4-(4-Acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanone

Product 1

HCID 578844724-(3-{[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-3H-thiazol-2-oneYield 6.1%

Procedure

Heat a solution of 1-(3-{[4-(4-acetyl-2-chloro-3-hydroxy-phenoxymethyl)-phenyl]-hydroxy-methyl}-phenyl)-2-chloro-ethanone (0.075 mg, 0.163 mmol) and potassium thiocyanate (159 mg, 1.63 mmol) in ethanol (0.20M) overnight at 70° C. Evaporate solvents and chromatograph residue. Major fraction isolated was the title compound (0.005 g, 0.010 mmol, 6.1%): 1H NMR (400 MHz, DMSO-d6) δ 2.61 (s, 3H), 5.10 (s, 2H), 5.30 (s, 2H), 5.82 (s, 1H), 6.11 (s, 1H), 6.88 (d, J=9.8 Hz, 1H), 7.41 (m, 4H), 7.49 (m, 1H), 7.71 (d, J=7.4 Hz, 1H), 7.87 (d, J=7.8 Hz, 1H), 7.92 (d, J=9.4 Hz, 1H), 8.04 (s, 1H), 13.12 (s, 1H). MS (m/z): 480 (M−H).

Workup

  1. customMajor fraction isolated

Sources & evidence

ORD record
ord-70f6904b9e5848478fe2eacbcee181f4
Source dataset
uspto-grants-2010_10
Patent number
US07816523B2

Reaction notes

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