Thionyl Chloride → HCID 19602322, compound

HRID 1604240Notes

Reaction equation

HRID 1604240 reaction equation
[CH3:1][Si:2]([CH3:16])([CH3:15])[C:3]1[S:4][C:5]2[CH:14]=[CH:13][CH:12]=[CH:11][C:6]=2[C:7]=1[C:8]([OH:10])=O.S(Cl)(Cl)=O.Cl.[CH:22]([NH:25][OH:26])([CH3:24])[CH3:23].C(=O)(O)[O-].[Na+]>C(Cl)Cl.O>[OH:26][N:25]([CH:22]([CH3:24])[CH3:23])[C:8]([C:7]1[C:6]2[CH:11]=[CH:12][CH:13]=[CH:14][C:5]=2[S:4][C:3]=1[Si:2]([CH3:1])([CH3:16])[CH3:15])=[O:10]

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 170873N-Isopropylhydroxylamine HydrochlorideHCID 516892Sodium BicarbonateHCID 22071497HCID 22071497, compound

Product 1

HCID 19602322HCID 19602322, compoundYield 66.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

A mixture of 2-(trimethylsilyl)-3-benzothiophenecarboxylic acid (0.8 g, 3.2 mmol), made as in Example 14, and thionyl chloride (6 mL) was refluxed for 2 h. The excess thionyl chloride was removed under reduced pressure. The crude acid chloride was dissolved in 20 mL methylene chloride and added to a mixture of N-isopropylhydroxylamine hydrochloride (0.4 g, 3.6 mmol) and 4 g sodium bicarbonate in 20 mL methylene chloride and 20 mL water at 0° C. The resulting mixture was stirred at RT for 2 h. The organic layer was separated, washed with brine, dried, and concentrated in vacuo. The crude product was chromatographed on a silica gel column with 10% ethyl acetate/hexane to give 0.65 g of the title compound as a yellow solid, a 66.1% yield. m.p. 115-118° C.

Workup

  1. temperaturewas refluxed for 2 h
  2. customThe excess thionyl chloride was removed under reduced pressure
  3. dissolutionThe crude acid chloride was dissolved in 20 mL methylene chloride
  4. customThe organic layer was separated
  5. washwashed with brine
  6. customdried
  7. concentrationconcentrated in vacuo
  8. customThe crude product was chromatographed on a silica gel column with 10% ethyl acetate/hexane

Sources & evidence

ORD record
ord-a657f6c5de644a53a3aeefdfe2380f9e
Source dataset
uspto-grants-1999_11
Patent number
US05994270

Reaction notes

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