Thionyl Chloride → HCID 86675000, compound

HRID 1908983Notes

Reaction equation

HRID 1908983 reaction equation
[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12]O)=[O:9])[CH:5]=[CH:4][CH:3]=1.O=S(Cl)[Cl:18]>C(Cl)(Cl)Cl>[NH2:1][C:2]1[N:7]=[C:6]([C:8]([NH:10][C:11]([CH3:15])([CH3:14])[CH2:12][Cl:18])=[O:9])[CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 71114856HCID 71114856, compound

Product 1

HCID 86675000HCID 86675000, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A solution of 6-amino-N-(1-hydroxy-2-methylpropan-2-yl)picolinamide (0.35 mmol, 74 mg) in CHCl3 was cooled to 0° C. and SOCl2 (2.8 mmol, 200 μL) was added. The mixture was refluxed overnight. After cooling to room temperature, the reaction was quenched with 1 M NaOH. The aqueous phase was extracted with CH2Cl2, and the combined organic phases were dried with MgSO4. The crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=2:1 as eluent). White solid, 76 mg, 95% yield. 1H NMR (500 MHz, CDCl3): 7.93 (br, 1H), 7.57-7.54 (m, 1H), 7.52-7.51 (m, 1H), 6.62 (d, 1H, J=8.0 Hz), 4.51 (br, 2H), 3.94 (s, 2H), 1.52 (s, 6H). 13C NMR (125 MHz, CDCl3): 163.97, 156.83, 148.37, 138.88, 112.33, 111.63, 53.72, 51.19, 25.08. MS (ESI, MeOH): 228 (100%, (M+1)+).

Workup

  1. temperatureThe mixture was refluxed overnight
  2. customthe reaction was quenched with 1 M NaOH
  3. extractionThe aqueous phase was extracted with CH2Cl2
  4. dry with materialthe combined organic phases were dried with MgSO4
  5. customThe crude product was purified by column chromatography on silica gel (Hexanes:ethyl acetate=2:1 as eluent)

Sources & evidence

ORD record
ord-4166ae9c20c74d3d9684428b9b3b2c9f
Source dataset
uspto-grants-2013_12
Patent number
US08598351B2

Reaction notes

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