Thionyl Chloride → HCID 57705602, compound

HRID 1662515Notes

Reaction equation

HRID 1662515 reaction equation
[CH:1]1([C:8]2[CH:13]=[C:12]([CH2:14]O)[CH:11]=[CH:10][C:9]=2[C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.S(Cl)([Cl:27])=O>C(Cl)Cl.CN(C=O)C>[Cl:27][CH2:14][C:12]1[CH:11]=[CH:10][C:9]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[CH:18][C:17]=2[F:24])=[C:8]([CH:1]2[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]2)[CH:13]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 57705618HCID 57705618, compound

Product 1

HCID 57705602HCID 57705602, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 78.7E (0.185 g, 0.6 mmol) in DCM (6 mL) and DMF (0.04 mL) at 0° C. was added thionyl chloride (0.08 mL, 1 mmol). The reaction was stirred at room temperature for one hour and then concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 78.7F as a colorless oil (0.165 g, 84% yield).

Workup

  1. concentrationconcentrated in vacuo
  2. customThe product was purified on silica gel (0-10% EtOAc in hexanes)

Sources & evidence

ORD record
ord-a416899b18f148c58bb4bda7d83c89dd
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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