Isopropanol → HCID 86665010, compound

HRID 468699Notes

Reaction equation

HRID 468699 reaction equation
S(Cl)([Cl:3])=O.Cl.[NH2:6][CH:7]([CH2:11][S:12][C:13]([CH3:16])([CH3:15])[CH3:14])[C:8]([OH:10])=[O:9].[CH3:17][CH:18](O)[CH3:19]>>[ClH:3].[CH:18]([O:9][C:8](=[O:10])[CH:7]([NH2:6])[CH2:11][S:12][C:13]([CH3:16])([CH3:15])[CH3:14])([CH3:19])[CH3:17]

Participants

4

Reactant 3

HCID 3776IsopropanolHCID 24386Thionyl ChlorideHCID 16219018HCID 16219018, compound

Product 1

HCID 86665010HCID 86665010, compoundYield 82%

Procedure

Thionyl chloride (20 mL) was added to a solution of 14 (20.0 g, 93.6 mmol) in i-PrOH (160 mL) at 0° C. slowly. The reaction mixture was refluxed for 4 h, then cooled and concentrated. The residue was treated with ether (200 mL). The resulting ppt was collected by filtration, washed with ether, and air-dried to provide 16 as a white solid (19.7 g, 82%). 1H NMR (400 MHz, DMSO-d6) δ 8.78 (br s, 3H), 5.00 (m, 1H), 4.14 (t, 1H), 3.03 (m, 2H), 1.29 (s, 9H), 1.26 (d, 3H), 1.24 (d, 3H).

Workup

  1. temperatureThe reaction mixture was refluxed for 4 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. additionThe residue was treated with ether (200 mL)
  5. filtrationThe resulting ppt was collected by filtration
  6. washwashed with ether
  7. customair-dried

Sources & evidence

ORD record
ord-79653aba5f65488493043a5d9434f917
Source dataset
uspto-grants-2014_01
Patent number
US08624052B2

Reaction notes

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