Water → 3-(5-Fluorobenzothiazol-2-yl-trans-ethenyl)benzaldehyde

HRID 1109775Notes

Reaction equation

[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[CH2:15][OH:16])=[N:7][C:6]=2[CH:20]=1.C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C.O>C(Cl)Cl.CS(C)=O.CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8](/[CH:10]=[CH:11]/[C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][CH:19]=3)[CH:15]=[O:16])=[N:7][C:6]=2[CH:20]=1

Participants

Conditions

Temperature: -60 °C

Procedure

To a solution of 1.5 g of 3-(5-fluorobenzothiazol-2-yl-trans-ethenyl)benzyl alcohol (Preparation H2) in 40 ml of methylene chloride and 25 ml of dimethylsulfoxide at -60° C. was added a solution of 0.64 ml of oxalyl chloride in 20 ml of dry methylene chloride containing 0.74 ml of dimethylsulfoxide. After stirring at -60° C. for 35 minutes the reaction mixture was allowed to warm to -35° C. for 25 minutes. The mixture was again cooled to -60° C. and 3.65 ml of triethylamine was added over a period of 5 minutes. The mixture was allowed to warm to room temperature and was treated with 200 ml of water. The organic phase was washed with a brine solution, dried over sodium sulfate and concentrated in vacuo to give after trituration with ethyl acetate--hexane 1.2 g. A sample was recrystallized from ethyl acetate--hexane, m.p. 151°-152° C.

Workup

temperatureto warm to -35° C. for 25 minutes
temperatureThe mixture was again cooled to -60° C.
temperatureto warm to room temperature
washThe organic phase was washed with a brine solution
dry with materialdried over sodium sulfate
concentrationconcentrated in vacuo
customto give after trituration with ethyl acetate
customA sample was recrystallized from ethyl acetate

Sources & evidence

ORD record: ord-32f639ec740048a38fecf01f25f12297
Source dataset: uspto-grants-1994_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05322847

Reaction notes

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