Sodium Iodide → 4(1H)-Pyridinone, 1,5-bis(diphenylmethoxy)-2-(hydroxymethyl)-

HRID 620750Notes

Reaction equation

[OH:1][N:2]1[CH:7]=[C:6]([O:8][CH:9]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:22])[CH:4]=[C:3]1[CH2:23][OH:24].C(=O)([O-])[O-].[K+].[K+].[I-].[Na+].[CH:33](Cl)([C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1)[C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>CS(C)=O>[CH:33]([O:1][N:2]1[CH:7]=[C:6]([O:8][CH:9]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)[C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:5](=[O:22])[CH:4]=[C:3]1[CH2:23][OH:24])([C:34]1[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1)[C:40]1[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=1

Participants

Conditions

Temperature: 100 °C

Procedure

8.1 g (0.0251 mol) of the product of Step (2) was added to dimethylsulfoxide (125 ml) and heated to 100° C. and dissolved. After cooling the solution to room temperature, 5.2 g (0.0375 mol) of potassium carbonate and 5.6 g (0.0375 mol) of sodium iodide and 6.7 ml (0.0375 mol) of benzhydrylchloride were added thereto, and the mixture was reacted at room temperature for 18 hours under stirring. To the reaction solution, ice water was gradually added, and formed precipitates were collected by filtration, washed sequentially with water and ethyl ether/n-hexane (2/1), and dried to obtain 12.3 g (yield: 100%) of the above identified compound.

Workup

dissolutiondissolved
temperatureAfter cooling the solution to room temperature
customthe mixture was reacted at room temperature for 18 hours
customformed
customprecipitates
filtrationwere collected by filtration
washwashed sequentially with water and ethyl ether/n-hexane (2/1)
customdried
customto obtain 12.3 g (yield: 100%) of the

Sources & evidence

ORD record: ord-6e75ba8a6cd64955a2afbfdd15dcfa17
Source dataset: uspto-grants-1989_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04822786

Reaction notes

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