Ammonium Chloride → HCID 66780948, compound

HRID 713604Notes

Reaction equation

HRID 713604 reaction equation
[F:1][C:2]1[C:10]([F:11])=[CH:9][C:5]2[NH:6][N:7]=[N:8][C:4]=2[CH:3]=1.CC(C)([O-])C.[K+].[CH2:18]([CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23]Br)[CH2:19][CH2:20][CH3:21].[NH4+].[Cl-]>CO>[CH2:18]([CH:22]([CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH3:30])[CH2:23][N:7]1[N:6]=[C:5]2[CH:9]=[C:10]([F:11])[C:2]([F:1])=[CH:3][C:4]2=[N:8]1)[CH2:19][CH2:20][CH3:21]

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 204476935-(Bromomethyl)undecaneHCID 23665647Potassium tert-butoxideHCID 178505412HCID 178505412, compound

Product 1

HCID 66780948HCID 66780948, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

5,6-difluoro-1H-benzo[d][1,2,3]triazole (8.04 g, 1.0 eq), potassium tert-butoxide (5.87 g, 1.01 eq), and 2-butyloctylbromide (13.04 g, 1.01 eq) were dissolved in 130 mL of methanol. The reaction was heated to reflux for 17 h. The reaction mixture was then poured into saturated NH4Cl solution, and extracted with ethyl acetate. The organic layer was washed with water (2×), dried (Na2SO4), filtered, concentrated in vacuo, and purified by column chromatography on silica gel using 10:1 hexanes:ethyl acetate as the eluent. Yield: 2.88 g (17%). Colorless oil. 1H NMR (CDCl3, 400 MHz, δ): 7.59 (t, 3JTHF=8.4 Hz, 2H), 4.58 (d, 3JHH=6.8 Hz, 2H), 2.22 (m, 1H), 1.28 (m, 16H), 0.86 (t, 3JHF=5.6 Hz, 6H).

Workup

  1. temperatureThe reaction was heated
  2. temperatureto reflux for 17 h
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with water (2×)
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. custompurified by column chromatography on silica gel using 10:1 hexanes

Sources & evidence

ORD record
ord-7da386f8754b4529898c5b9f2d1e1fc9
Source dataset
uspto-grants-2015_11
Patent number
US09184390B2

Reaction notes

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