Thionyl Chloride → HCID 15052150, compound

HRID 973439Notes

Reaction equation

HRID 973439 reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH2:11][CH:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]1=[O:27]>C(Cl)Cl>[Cl:3][CH2:6][CH2:7][N:8]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12][CH2:11][CH:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH3:26])=[CH:21][CH:20]=2)[C:9]1=[O:27]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15052149HCID 15052149, compound

Product 1

HCID 15052150HCID 15052150, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

0.14 ml of thionyl chloride was added to a solution of 329 mg of the product of Step C in 3.3 ml of methylene chloride and the mixture was stirred for 15 minutes at ambient temperature, then evaporated to dryness under reduced pressure. The residue was taken up in 25 ml of ether at reflux, treated with activated charcoal, filtered and concentrated to 7 ml. After separation, 300 mg of the expected product melting at approx. 70° C. were obtained which was used as is for Step E. An analytical sample was prepared by dissolving 300 mg of the product in 10 ml of hot methyl ethyl ketone which was concentrated to 2 ml, then adding 2 ml of pentane. After separating, 65 mg of the desired product melting at approx. 70° C. were obtained.

Workup

  1. customevaporated to dryness under reduced pressure
  2. temperatureat reflux
  3. additiontreated with activated charcoal
  4. filtrationfiltered
  5. concentrationconcentrated to 7 ml
  6. customAfter separation

Sources & evidence

ORD record
ord-04c632c0ae0c4b9ebd1549cefd6caf6c
Source dataset
uspto-grants-1991_11
Patent number
US05063225

Reaction notes

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