Hydrochloric Acid → 3-[2,4-Dichloro-6-fluorobenzothiazol-7-yl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

HRID 1419706Notes

Reaction equation

[H-].[Na+].[NH2:3][C:4]([C:12]([F:15])([F:14])[F:13])=[CH:5][CH2:6]C(OCC)=O.[Cl:16][C:17]1[S:18][C:19]2[C:25]([N:26]=[C:27]=[O:28])=[C:24]([F:29])[CH:23]=[C:22]([Cl:30])[C:20]=2[N:21]=1.Cl.CN(C)C=[O:35]>O1CCCC1>[Cl:16][C:17]1[S:18][C:19]2[C:25]([N:26]3[C:6](=[O:35])[CH:5]=[C:4]([C:12]([F:13])([F:14])[F:15])[NH:3][C:27]3=[O:28])=[C:24]([F:29])[CH:23]=[C:22]([Cl:30])[C:20]=2[N:21]=1

Participants

Conditions

Temperature: -30 °C

Procedure

1.6 g of sodium hydride (97% strength) in 200 ml of absolute dimethylformamide were initially taken. 11.0 g of ethyl 3-amino-4,4,4-trifluorobut-2-enecarboxylate were then added dropwise at from 0° to 5° C. Stirring was carried out for one hour at this temperature, after which the mixture was cooled to -30° C. and 16.2 g of 2,4-dichloro-6-fluoro-7-isocyanatobenzothiazole in 50 ml of absolute tetrahydrofuran were then added dropwise. The mixture was stirred for one hour at this temperature and then slowly warmed up to room temperature. Thereafter, ice water was added and the pH was brought to 3-4 with dilute hydrochloric acid, after which the product was extracted with ethyl acetate. The ester solution was dried and then evaporated down.

Workup

stirringThe mixture was stirred for one hour at this temperature
temperatureslowly warmed up to room temperature
extractionafter which the product was extracted with ethyl acetate
dry with materialThe ester solution was dried
customevaporated down

Sources & evidence

ORD record: ord-a5d3fbc8e7f243e58666a6a5d172497f
Source dataset: uspto-grants-1999_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05888940

Reaction notes

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