Hydrochloric Acid → HCID 18690191, compound

HRID 328536Notes

Reaction equation

HRID 328536 reaction equation
C(S)C.[H-].[Na+].C[O:7][C:8]1[CH:33]=[CH:32][C:11]([C:12]([C:14]2[CH2:15][CH2:16][C:17]3[C:22]([C:23]=2[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[CH:21][CH:20]=[C:19]([O:30]C)[CH:18]=3)=[O:13])=[CH:10][CH:9]=1.Cl>CN(C=O)C>[OH:7][C:8]1[CH:33]=[CH:32][C:11]([C:12]([C:14]2[CH2:15][CH2:16][C:17]3[C:22]([C:23]=2[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)=[CH:21][CH:20]=[C:19]([OH:30])[CH:18]=3)=[O:13])=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6343EthanethiolHCID 24758Sodium hydride2×HCID 18690204HCID 18690204, compound

Product 1

HCID 18690191HCID 18690191, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

To 300 ml. of DMF were added under nitrogen and with ice bath cooling, 9.3 gms. of ethyl mercaptan. To the mixture then were added 7.2 gms. of 50 percent sodium hydride-oil mixture. The mixture represents 0.15 mole of sodium hydride. To the resulting mixture then were added 11.1 gms. (0.03 mole) of the product from Example 4. The mixture was heated at 60° C. for 1 hour. Analysis of the reaction mixture by TLC indicated the presence of starting material plus another component, probably the mono-hydroxy compound. The temperature of the reaction mixture was raised to 110° C., and this temperature was maintained for 1 hour. TLC showed no starting material; however, the presence of two components was noted. The reaction mixture therefore was heated for an additional 1 hour at 125° C. after which a single spot was noted by TLC analysis. The reaction mixture then was acidified by addition of cold 1N hydrochloric acid. The mixture was extracted with ethyl acetate. The ethyl acetate was washed with water and evaporated. The resulting residue was recrystallized from a mixture of methanol and acetone to give 8 g. of the title compound, m.p. 205°-207° C.

Workup

  1. temperaturecooling
  2. additionTo the mixture then were added 7.2 gms
  3. additionTo the resulting mixture then were added 11.1 gms
  4. temperatureThe temperature of the reaction mixture was raised to 110° C.
  5. temperaturethis temperature was maintained for 1 hour
  6. temperatureThe reaction mixture therefore was heated for an additional 1 hour at 125° C. after which a single spot
  7. extractionThe mixture was extracted with ethyl acetate
  8. washThe ethyl acetate was washed with water
  9. customevaporated
  10. customThe resulting residue was recrystallized from a mixture of methanol and acetone
  11. customto give 8 g

Sources & evidence

ORD record
ord-04fc967147c342908d01d7e59ae65464
Source dataset
uspto-grants-1977_04
Patent number
US04017546

Reaction notes

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