Hydrochloric Acid → HCID 54057778, compound

HRID 1419718Notes

Reaction equation

HRID 1419718 reaction equation
[C:1]([O:5][CH2:6][CH3:7])(=[O:4])[CH:2]=[CH2:3].N(OC(C)(C)C)=O.N[C:16]1[S:17][C:18]2[CH:24]=[C:23]([F:25])[CH:22]=[C:21]([Cl:26])[C:19]=2[N:20]=1.Cl>[Cu](Cl)Cl.C(#N)C>[Cl:26][C:21]1[C:19]2[N:20]=[C:16]([CH:3]=[CH:2][C:1]([O:5][CH2:6][CH3:7])=[O:4])[S:17][C:18]=2[CH:24]=[C:23]([F:25])[CH:22]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 8821Ethyl AcrylateHCID 10906Tert-Butyl nitriteHCID 121544622-Amino-4-chloro-6-fluorobenzothiazole

Product 1

HCID 54057778HCID 54057778, compound

Reagents, catalysts & solvents 2

HCID 24014Cupric ChlorideCatalystHCID 6342AcetonitrileSolvent

Procedure

150 g (1.48 mol) of ethyl acrylate, 11.4 g (85 mmol) of copper (II) chloride and 11.4 g (0.11 mol) of tert-butyl nitrite were added to a solution of 12 g (59 mmol) of 2-amino-4-chloro-6-fluorobenzothiazole in 0.4 1 of acetonitrile. Stirring was carried out for 3 days, after which the mixture was acidified with dilute hydrochloric acid. The product was extracted with methyl tert-butyl ether, after which the extracts were dried over magnesium sulfate and finally evaporated down. Purification of the crude product was effected by means of column chromatography over silica gel (eluent: 19:1 cyclohexane/methyl tert-butyl ether). Yield: 9,0 g.

Workup

  1. extractionThe product was extracted with methyl tert-butyl ether
  2. dry with materialafter which the extracts were dried over magnesium sulfate
  3. customfinally evaporated down
  4. customPurification of the crude product

Sources & evidence

ORD record
ord-afe153120f714492b189900ad97e0b55
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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