Dimethylformamide → HCID 18318497, compound

HRID 2163318Notes

Reaction equation

HRID 2163318 reaction equation
CN(C=O)C.[N:6]1([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][C:22]4[CH:38]=[CH:37][CH:36]=[CH:35][C:23]=4[C:24]=3[C:25](=[O:34])[C:26]3[CH:31]=[CH:30][C:29]([O:32]C)=[CH:28][CH:27]=3)=[CH:16][CH:15]=2)[CH2:10][CH2:9][CH2:8][CH2:7]1.[H-].[Na+].C(S)C>C(O)C>[N:6]1([CH2:11][CH2:12][O:13][C:14]2[CH:19]=[CH:18][C:17]([C:20]3[S:21][C:22]4[CH:38]=[CH:37][CH:36]=[CH:35][C:23]=4[C:24]=3[C:25](=[O:34])[C:26]3[CH:31]=[CH:30][C:29]([OH:32])=[CH:28][CH:27]=3)=[CH:16][CH:15]=2)[CH2:7][CH2:8][CH2:9][CH2:10]1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6343EthanethiolHCID 24758Sodium hydrideHCID 18318460HCID 18318460, compound

Product 1

HCID 18318497HCID 18318497, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
75 °C

Procedure

To 50 ml. of dry DMF were added 1.2 g. (2.6 mmole) of the product from Example 16. Sodium hydride (625 mg.; 26 mmole) was added to the mixture under a nitrogen atmosphere. To the resulting mixture then were slowly added by syringe 620 mg. (10 mmole) of ethyl mercaptan. A vigorous effervescence occurred. When the effervescence had ceased, the reaction mixture was heated at 75° C. in an oil bath for 12 hours. Ethanol (5 ml.) then was added dropwise. The resulting mixture was evaporated to dryness, and the residue was dissolved in a mixture of ethyl acetate and water. The ethyl acetate layer was separated, washed with 50 ml. of aqueous sodium chloride solution, and then repeatedly with 15 ml. portions of 1N hydrochloric acid. The hydrochloric acid extracts were combined, washed with ether, and rendered alkaline by addition of cold 1N sodium hydroxide. The alkaline mixture then was extracted with ethyl acetate, and the ethyl acetate extract, after drying over magnesium sulfate, was evaporated to obtain 0.54 g. of a yellow oil. The yellow oil was chromatographed to obtain 400 mg. of the title compound as a yellow foam.

Workup

  1. additionTo the resulting mixture then were slowly added by syringe 620 mg
  2. customThe resulting mixture was evaporated to dryness
  3. dissolutionthe residue was dissolved in a mixture of ethyl acetate and water
  4. customThe ethyl acetate layer was separated
  5. washwashed with 50 ml
  6. washwashed with ether
  7. additionby addition of cold 1N sodium hydroxide
  8. extractionThe alkaline mixture then was extracted with ethyl acetate
  9. extractionthe ethyl acetate extract
  10. dry with materialafter drying over magnesium sulfate
  11. customwas evaporated
  12. customto obtain 0.54 g
  13. customThe yellow oil was chromatographed
  14. customto obtain 400 mg

Sources & evidence

ORD record
ord-6f13d48a65e04d1283439f30cb978a08
Source dataset
uspto-grants-1979_01
Patent number
US04133814

Reaction notes

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