Carbon Dioxide → HCID 21997486, compound

HRID 1977301Notes

Reaction equation

C(O[C:9]1[CH:14]=[CH:13][C:12]([C:15]2[S:16][C:17]([C:20]3[CH:25]=[CH:24][C:23](Br)=[CH:22][CH:21]=3)=[CH:18][N:19]=2)=[CH:11][CH:10]=1)CCCCCC.[CH2:27]([Li])[CH2:28][CH2:29]C.[C:32](=[O:34])=[O:33].Cl.[O:36]1[CH2:40][CH2:39][CH2:38][CH2:37]1>CCCCCC.O>[CH2:37]([O:36][C:23]1[CH:22]=[CH:21][C:20]([C:17]2[S:16][C:15]([C:12]3[CH:11]=[CH:10][C:9]([C:32]([OH:34])=[O:33])=[CH:14][CH:13]=3)=[N:19][CH:18]=2)=[CH:25][CH:24]=1)[CH2:38][CH2:39][CH2:40][CH2:27][CH2:28][CH3:29]

Participants

Conditions

Temperature: -60 °C

Procedure

A solution of 2-(4-heptyloxyphenyl)-5-(4-bromophenyl)thiazole (2.06 g) in dry tetrahydrofuran (60 ml) was cooled to −60° C., and a solution of n-butyllithium (1.56M) in n-hexane, 4.05 ml) was added slowly to maintain the reaction temperature at −60° C. After stirring for 1 hour, dry-ice (4 g) was added. The reaction mixture was allowed to warm to room temperature over 30 minutes. To the reaction mixture was added water (20 ml) and 0.5N hydrochloric acid (80 ml), then extracted with dichloromethane (700 ml). The organic layer was washed with brine, and dried over magnesium sulfate. Magnesium sulfate was filtered off, and the filtrate was evaporated under reduced pressure. The solids were slurried in acetonitrile and collected by filtration to give 4-[5-(4-heptyloxyphenyl)thiazol-2-yl]benzoic acid (1.68 g).

Workup

temperatureto warm to room temperature over 30 minutes
extractionextracted with dichloromethane (700 ml)
washThe organic layer was washed with brine
dry with materialdried over magnesium sulfate
filtrationMagnesium sulfate was filtered off
customthe filtrate was evaporated under reduced pressure
filtrationcollected by filtration

Sources & evidence

ORD record: ord-5c5bdfd4dc97433e9b35edbf2c7958b5
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06232290B1

Reaction notes

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