Thionyl Chloride → HCID 18630389, compound

HRID 378086Notes

Reaction equation

HRID 378086 reaction equation
[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH2:11]O)=[O:8])=[C:4]([Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1.S(Cl)([Cl:19])=O>C(Cl)Cl>[Cl:1][C:2]1[S:6][C:5]([C:7]([NH:9][CH2:10][CH2:11][Cl:19])=[O:8])=[C:4]([Si:13]([CH3:16])([CH3:15])[CH3:14])[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 18630300HCID 18630300, compound

Product 1

HCID 18630389HCID 18630389, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of the compound of Example 263 (0.4 g) and 1 mL thionyl chloride in 6 mL CH2Cl2 was refluxed for 1 h, then cooled and poured into ice-water. Additional CH2Cl2 was added. The organic layer was separated, washed with brine, dried and concentrated. Flash chromatography of the residue with 5% ethyl acetate-hexane as eluent gave 0.4 g of the desired product as a white solid. m.p. 68-72° C.

Workup

  1. temperaturecooled
  2. customThe organic layer was separated
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-fa82b56ac8e04d4fb5440dd3e06737fd
Source dataset
uspto-grants-2000_02
Patent number
US06028101

Reaction notes

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