Sodium Chloride → HCID 7854344, compound

HRID 1954391Notes

Reaction equation

[H-].[Na+].[SH:3][C:4]1[S:5][C:6]2[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=2[N:8]=1.Br[CH2:17][C:18]1[CH:25]=[CH:24][C:21]([C:22]#[N:23])=[CH:20][CH:19]=1.[Cl-].[Na+]>C(OCC)(=O)C>[C:22]([C:21]1[CH:24]=[CH:25][C:18]([CH2:17][S:3][C:4]2[S:5][C:6]3[CH:12]=[C:11]([N+:13]([O-:15])=[O:14])[CH:10]=[CH:9][C:7]=3[N:8]=2)=[CH:19][CH:20]=1)#[N:23]

Participants

Conditions

Temperature: 50 °C

Procedure

0.37 g (7.7 mmol) of sodium hydride (50% in mineral oil) is added batchwise to a solution of 1.5 g (7.06 mmol) of 2-mercapto-6-nitro-benzothiazole and then stirred for 30 minutes at 50° C. Then 1.45 g (7.4 mmol) of 4-bromomethylbenzonitrile is added dropwise and stirred for a further hour at 50° C. The re-action mixture is mixed with 30 ml of ethyl acetate and 70 ml of 14% sodium chloride solution, whereupon a large proportion of the title compound is obtained as a beige precipitate. The organic phase is concentrated in vacuo, the crude product precipitated is triturated with diethyl ether and the liquid phase is separated off. The solid obtained is combined with the beige precipitate.

Workup

stirringstirred for a further hour at 50° C

Sources & evidence

ORD record: ord-e0d047b5d75249cf91aa0731f103720a
Source dataset: uspto-grants-2000_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06121308

Reaction notes

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