Hydrochloric Acid → HCID 15754357, compound

HRID 1084651Notes

Reaction equation

HRID 1084651 reaction equation
[H-].[Na+].C(S)C.[Cl:6][C:7]1[CH:8]=[C:9]([CH:26]=[C:27]([Cl:31])[C:28]=1[O:29]C)[C:10]([N:13]1[CH2:17][C:16]([CH3:18])=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]1=[O:25])([CH3:12])[CH3:11].Cl>CN(C=O)C>[Cl:6][C:7]1[CH:8]=[C:9]([CH:26]=[C:27]([Cl:31])[C:28]=1[OH:29])[C:10]([N:13]1[CH2:17][C:16]([CH3:18])=[C:15]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[C:14]1=[O:25])([CH3:12])[CH3:11]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 15754307HCID 15754307, compound

Product 1

HCID 15754357HCID 15754357, compoundYield 73.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Conditions

Temperature
10 °C

Procedure

A DMF suspension of 2.2 g (0.05 mol) of sodium hydride (about 60% in oil) was cooled with ice water, and 5.1 g (0.05 mol) of ethyl mercaptan was dropwise added thereto at a temperature not higher than 10° C. under stirring. The reaction mixture was returned to room temperature and left to stand for about 30 minutes. Then, a DMF solution of 15.7 g (0.04 mol) of 1-(3,5- dichloro-4-methoxy-α,α-dimethylbenzyl)-4-methyl-3-phenyl- 3-pyrrolin-2-one (Compound No. 143) prepared in Example 2, was added thereto. The solution was heated at about 80° C. and reacted for three hours. After completion of the reaction, the reaction solution was poured into a large amount of ice water, acidified with a 10% hydrochloric acid aqueous solution and then extracted with ethyl acetate. The ethyl acetate layer was dried over anhydrous magnesium sulfate, and then the solvent was distilled off under reduced pressure. The solid thereby obtained was washed with isopropyl ether to obtain 11.0 g (yield: 73.3%) of the desired compound as colorless crystals.

Workup

  1. additionwas dropwise added
  2. customwas returned to room temperature
  3. waitleft
  4. custom143) prepared in Example 2
  5. additionwas added
  6. temperatureThe solution was heated at about 80° C.
  7. customreacted for three hours
  8. customAfter completion of the reaction
  9. extractionextracted with ethyl acetate
  10. dry with materialThe ethyl acetate layer was dried over anhydrous magnesium sulfate
  11. distillationthe solvent was distilled off under reduced pressure
  12. customThe solid thereby obtained
  13. washwas washed with isopropyl ether

Sources & evidence

ORD record
ord-5b9e44ac2f1445b89570066876c83131
Source dataset
uspto-grants-1991_04
Patent number
US05006157

Reaction notes

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