Thionyl Chloride → HCID 88456965, compound

HRID 1729106Notes

Reaction equation

HRID 1729106 reaction equation
[CH3:1][CH:2]1[C:6]([CH3:7])=[C:5]([CH2:8]O)[C:4](=[S:10](=[O:12])=[O:11])[N:3]1[C:13]1[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=1.O=S(Cl)[Cl:22]>C1(C)C=CC=CC=1>[Cl:22][CH2:8][C:5]1[C:4](=[S:10](=[O:12])=[O:11])[N:3]([C:13]2[CH:18]=[CH:17][C:16]([CH3:19])=[CH:15][CH:14]=2)[CH:2]([CH3:1])[C:6]=1[CH3:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 88456901HCID 88456901, compound

Product 1

HCID 88456965HCID 88456965, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

To a stirred solution of the alcohol from Step 2 (6.8 g, 24.3 mmo 1 ) in dry toluene (70 mL) was added dropwise SOCl2 (9.5 mL) and the mixturewas stirred for 3 hours at room temperature. The excess of SOCl2 and the solvent were removed in vacuo and the residue partitioned between water (10 mL) and diethyl ether (100 mL). The organic phase was separated,dried (NaSO4), and concentrated in vacuo to give the required compoundas a brown solid, m.p. 105°-109° C., which was used without further purification.

Workup

  1. customThe excess of SOCl2 and the solvent were removed in vacuo
  2. customthe residue partitioned between water (10 mL) and diethyl ether (100 mL)
  3. concentrationconcentrated in vacuo
  4. customto give the required compoundas a brown solid, m.p. 105°-109° C., which
  5. customwas used without further purification

Sources & evidence

ORD record
ord-52f26ae268334e0fbcb895cfcdb1940c
Source dataset
uspto-grants-1994_07
Patent number
US05331006

Reaction notes

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