Dimethylformamide → HCID 57706950, compound

HRID 1662491Notes

Reaction equation

HRID 1662491 reaction equation
CC([Si](C)(C)O[CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]([OH:30])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:9]=1)(C)C.CN(C=O)C.S(Cl)([Cl:40])=O>C(Cl)Cl>[Cl:40][CH2:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:19]=[C:18]([O:20][CH3:21])[CH:17]=[CH:16][C:15]=2[F:22])=[C:10]([C:23]([OH:30])([CH:27]([CH3:29])[CH3:28])[CH:24]([CH3:26])[CH3:25])[CH:9]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 57705817HCID 57705817, compound

Product 1

HCID 57706950HCID 57706950, compoundYield 109.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a stirred solution of 69.19B (0.050 g, 0.1 mmol) in DCM (2.00 mL) at 23° C. was added DMF (0.0008 mL) followed by thionyl chloride (0.01 mL, 0.2 mmol). The reaction was then stirred for 1.5 hours and then concentrated in vacuo. The product was purified on silica gel (0-10% EtOAc in hexanes) to yield 69.19C as a colorless oil (0.04 g, 100% yield).

Workup

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

Sources & evidence

ORD record
ord-91caa0a1835f4e8fa3a78c1ab1c6a044
Source dataset
uspto-grants-2011_10
Patent number
US08030354B2

Reaction notes

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