Thionyl Chloride → HCID 21262817, compound

HRID 567949Notes

Reaction equation

HRID 567949 reaction equation
[F:1][CH:2]([F:33])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:16]2[CH:17]=[N:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)O)[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12].CCN(C(C)C)C(C)C.O=S(Cl)[Cl:45]>C1(C)C=CC=CC=1>[F:1][CH:2]([F:33])[O:3][C:4]1[CH:5]=[C:6]([CH:14]([C:16]2[CH:17]=[N:18][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([C:29]([O:31][CH3:32])=[O:30])=[CH:25][CH:24]=3)=[CH:20][CH:21]=2)[Cl:45])[CH:7]=[CH:8][C:9]=1[O:10][CH:11]([F:13])[F:12]

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 21262815HCID 21262815, compound

Product 1

HCID 21262817HCID 21262817, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of alcohol (535 mg, 1.14 mmol) from step 2 and i-Pr2NEt (436 mL, 2.5 mmol) in 10 mL of anhydrous toluene, was slowly added SOCl2 (145 mnL, 2.0 mmol). The resulting yellow solution was stirred 30 minutes at 0° C., 10 minutes at room temperature, quenched with water and diluted with ethyl acetate. The organic layer was washed with brine, dried over MgSO4 and concentrated under reduced pressure. The residue was used directly for the next step without any purification.

Workup

  1. customTo a 0° C.
  2. customquenched with water
  3. additiondiluted with ethyl acetate
  4. washThe organic layer was washed with brine
  5. dry with materialdried over MgSO4
  6. concentrationconcentrated under reduced pressure
  7. customThe residue was used directly for the next step without any purification

Sources & evidence

ORD record
ord-93f3a2912b6346efbf04f2f85c261ad9
Source dataset
uspto-grants-2001_01
Patent number
US06180650B2

Reaction notes

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