Water → HCID 3528238, compound

HRID 1942988Notes

Reaction equation

HRID 1942988 reaction equation
[CH3:1][C:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([NH2:10])[CH:5]=1)=[O:3].C(N(CC)CC)C.[C:18](Cl)(=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20].O>C(Cl)(Cl)Cl>[C:2]([C:4]1[CH:5]=[C:6]([NH:10][C:18](=[O:23])[C:19]([CH3:22])([CH3:21])[CH3:20])[CH:7]=[CH:8][CH:9]=1)(=[O:3])[CH3:1]

Participants

6

Reactant 4

HCID 962WaterHCID 74173'-AminoacetophenoneHCID 8471TriethylamineHCID 62493Pivaloyl chloride

Product 1

HCID 3528238HCID 3528238, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a stirred solution of 3-aminoacetophenone (1.0 g, 7.4 mmol) in chloroform cooled to 0° C. was added triethylamine dropwise (1.44 g, 14.2 mmol). The mixture was stirred for 15 min at this temperature and then pivaloyl chloride (0.83 g, 7.4 mmol) was added dropwise and the mixture was stirred overnight. Water was added and the aqueous layer was extracted with DCM. The collected organic extracts were washed with sat. aq. NaHCO3 and brine, dried over anhydrous MgSO4, and filtered. The solvent was evaporated under reduced pressure to afford 8z as a white solid (1.29 g, 80%). Mp 130-133° C. 1H NMR (600 MHz, CDCl3): δ 8.07 (t, J=1.8 Hz, 1H), 7.90-7.88 (m, 1H), 7.76 (br s, 1H), 7.65-7.63 (m, 1H), 7.37 (t, J=1.8 Hz 1H), 2.57 (s, 3H), 1.31 (s, 9H). 13C NMR (150 MHz, CDCl3): δ 198.2, 177.2, 138.8, 137.7, 129.3, 124.9, 124.1, 119.7, 39.8, 27.6, 26.8.

Workup

  1. stirringthe mixture was stirred overnight
  2. extractionthe aqueous layer was extracted with DCM
  3. washThe collected organic extracts were washed with sat. aq. NaHCO3 and brine
  4. dry with materialdried over anhydrous MgSO4
  5. filtrationfiltered
  6. customThe solvent was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d5fec8cbf1464ae18615d22cc3df878b
Source dataset
uspto-grants-2013_03
Patent number
US08389736B2

Reaction notes

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