Hydrochloric Acid → HCID 14820154, compound

HRID 2166394Notes

Reaction equation

HRID 2166394 reaction equation
[C:1]([C:4]1[CH:9]=[C:8]([CH2:10]O)[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:6][C:5]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])(=[O:3])[CH3:2].N1C(C)=CC(C)=CC=1C.[Cl-].[Li+].CS([Cl:41])(=O)=O.Cl.[Cl-].[Na+]>CN(C)C=O>[C:1]([C:4]1[CH:9]=[C:8]([CH2:10][Cl:41])[C:7]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][C:17]#[N:18])=[CH:6][C:5]=1[O:19][CH2:20][CH2:21][CH2:22][CH2:23][C:24]#[N:25])(=[O:3])[CH3:2]

Participants

8

Reactant 6

HCID 313Hydrochloric AcidHCID 5234Sodium ChlorideHCID 79532,4,6-TrimethylpyridineHCID 31297Methanesulfonyl chlorideHCID 433294Lithium ChlorideHCID 14820151HCID 14820151, compound

Product 1

HCID 14820154HCID 14820154, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound of Example 124 (688 mg) was dissolved in 50 ml of dimethylformamide. To this solution were added 0.29 ml of collidine followed by 0.252 g of lithium chloride. The reaction was cooled by means of an external ice bath and 0.507 ml of methane sulfonyl chloride were added. After stirring for 2 hours, the reaction was allowed to warm to room temperature. The mixture was poured into cold dilute hydrochloric acid to which sodium chloride had been added and the solution was extracted with ethyl acetate. The organic layer was washed twice with cold hydrochloric acid/sodium chloride, dried over sodium sulfate, and concentrated in vacuo. Concentration of the solution provided a residue which was crystallized from methylene chloride/hexane to provide 180 mg of the desired title product, m.p.=100°-110° C. (decomposition).

Workup

  1. temperatureThe reaction was cooled by means of an external ice bath
  2. additionhad been added
  3. extractionthe solution was extracted with ethyl acetate
  4. washThe organic layer was washed twice with cold hydrochloric acid/sodium chloride
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customConcentration of the solution provided a residue which
  8. customwas crystallized from methylene chloride/hexane

Sources & evidence

ORD record
ord-91964960f692402ea597c474d5823f2b
Source dataset
uspto-grants-1990_07
Patent number
US04945099

Reaction notes

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