Hydrochloric Acid → HCID 53966919, compound

HRID 1419716Notes

Reaction equation

HRID 1419716 reaction equation
[Br-:1].[Na+].N[C:4]1[S:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[C:7]=2[N:8]=1.N(OC(C)(C)C)=O.Cl>[Cu]Br.C(#N)C>[Br:1][C:4]1[S:5][C:6]2[CH:12]=[C:11]([Cl:13])[CH:10]=[C:9]([Cl:14])[C:7]=2[N:8]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10906Tert-Butyl nitriteHCID 1127224,6-Dichloro-1,3-benzothiazol-2(3H)-imineHCID 253881Sodium Bromide

Product 1

HCID 53966919HCID 53966919, compound

Reagents, catalysts & solvents 2

HCID 24593copper(I) bromideCatalystHCID 6342AcetonitrileSolvent

Procedure

35 g (0.24 mol) of copper(I) bromide and 126 g (1.23 mol) of sodium bromide were added to a solution of 27 g (0.12 mol) of 2-amino-4,6-dichlorobenzothiazole in 0.5 1 of acetonitrile, and 16.5 g (0.16 mol) of tert-butyl nitrite were then added dropwise. Stirring was carried out for 16 hours, after which the reaction mixture was acidified with 10% strength hydrochloric acid. The product was then extracted with methyl tert-butyl ether. The organic phase was washed with water, dried over magnesium sulfate and finally evaporated down. Purification of the crude product was carried out by means of column chromatography over silica gel (eluent: 1:1 cyclohexane/ethyl acetate). Yield: 9.1 g.

Workup

  1. additionwere then added dropwise
  2. extractionThe product was then extracted with methyl tert-butyl ether
  3. washThe organic phase was washed with water
  4. dry with materialdried over magnesium sulfate
  5. customfinally evaporated down
  6. customPurification of the crude product

Sources & evidence

ORD record
ord-bb9b974847924fa3aea17c3b8330233b
Source dataset
uspto-grants-1999_03
Patent number
US05888940

Reaction notes

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