Acetonitrile → HCID 68802901, compound

HRID 1430393Notes

Reaction equation

HRID 1430393 reaction equation
C(#N)C.N(OC(C)(C)C)=O.N[C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:16]=1.C(Cl)(Cl)[Cl:24].CCCCCC>[Cu](Cl)Cl>[Cl:24][C:12]1[S:13][CH:14]=[C:15]([CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])[N:16]=1

Participants

6

Reactant 4

HCID 6342Acetonitrile2×HCID 10906Tert-Butyl nitriteHCID 139342624-Hexyl-1,3-thiazol-2-amineHCID 21585165Chloroform hexane

Product 1

HCID 68802901HCID 68802901, compound

Reagents, catalysts & solvents 1

HCID 24014Cupric ChlorideCatalyst

Procedure

To 200 mL of acetonitrile was added 9.7 mL (81 mmol) of t-butyl nitrite and 8.75 g (65.1 mmol) of copper(II) chloride, and 10 mL of acetonitrile containing 10.0 g (54.3 mmol) of 2-amino-4-hexylthiazole (Helvetica Chemica Acta XXXII, Fasciculus I, 35 (1949)) dissolved therein was added to this portion-wise while cooling with ice under an argon atmosphere and the temperature thereof was returned to room temperature and the mixture was stirred for 2 hours. Then, the resultant reaction mixed liquid was poured into 100 ml of chloroform/hexane mixed liquid, and the precipitate was removed by filtration. The filtrate was washed with 100 ml of a 20 wt % hydrochloric acid aqueous solution three times, then, extracted with chloroform. The resultant extraction liquid was dried over anhydrous magnesium sulfate, then, concentrated under reduced pressure, and purified by silica gel column chromatography (development solvent:chloroform/hexane=1/1 (volumetric ratio)), to obtain the intended 2-chloro-4-hexylthiazole.

Workup

  1. dissolutiondissolved
  2. additiontherein was added to this portion-wise
  3. temperaturewhile cooling with ice under an argon atmosphere
  4. customthereof was returned to room temperature
  5. customThen, the resultant reaction
  6. additionmixed liquid
  7. customthe precipitate was removed by filtration
  8. washThe filtrate was washed with 100 ml of a 20 wt % hydrochloric acid aqueous solution three times
  9. extractionextracted with chloroform
  10. extractionThe resultant extraction liquid
  11. dry with materialwas dried over anhydrous magnesium sulfate
  12. concentrationconcentrated under reduced pressure
  13. custompurified by silica gel column chromatography (development solvent:chloroform/hexane=1/1 (volumetric ratio))

Sources & evidence

ORD record
ord-77511e3214d9495aaaf6d80bf7691d60
Source dataset
uspto-grants-2015_01
Patent number
US08940856B2

Reaction notes

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