Methane → Ethanethioamide, N-(4-methoxy-3-methylphenyl)-

HRID 462485Notes

Reaction equation

HRID 462485 reaction equation
[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([CH3:11])=O)[CH:5]=[CH:4][C:3]=1[O:12][CH3:13].P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:15].[OH-].[Na+].C.Cl>O.O1CCOCC1.N1C=CC=CC=1>[CH3:1][C:2]1[CH:7]=[C:6]([NH:8][C:9]([CH3:11])=[S:15])[CH:5]=[CH:4][C:3]=1[O:12][CH3:13]

Participants

9

Reactant 5

HCID 297MethaneHCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 14817Phosphorus sulfide (P2S5)HCID 4004288HCID 4004288, compound

Product 1

HCID 3034997Ethanethioamide, N-(4-methoxy-3-methylphenyl)-

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 1049PyridineSolventHCID 312751,4-DioxaneSolvent

Procedure

185 g of 2-methyl-4-acetamino-anisole (prepared by procedures described by M. Heidelberg and W. A. Jacobs in J.A.C.S. 41 (1919) p. 1453), 100 ml of pyridine and 250 ml of anhydrous dioxane were poured into a 1 l. multi-neck flask mounted on an oil bath whose temperature was 100° C. After complete dissolution, 130 g of P2S5 were added thereto in small portions under stirring; after the addition, the solution thus obtained was stirred for another 45 minutes by maintaining the conditions of the reaction temperature. The reaction mixture was poured into a 5 l. of a very cold water solution of 45 g of NaOH; animal charcoal was added thereto and the whole stirred for 1 hour. After filtration, the solution was poured into a Keller flask, provided with a stirrer and externally cooled, cautiously acidified with concentrated HCl to pH=4-5, keeping the temperature lower than +5° C. After approximately 1 hour of stirring, the product, thus separated, was filtered with a Buchner and washed with water. The raw product was crystallized many times from ligroin in the presence of animal charcoal to reach a melting point of 88.5°-89° C.

Workup

  1. custommulti-neck flask mounted on an oil bath
  2. customwas 100° C
  3. additionwere added
  4. additionafter the addition
  5. customthe solution thus obtained
  6. stirringwas stirred for another 45 minutes
  7. temperatureby maintaining the conditions of the reaction temperature
  8. additionThe reaction mixture was poured into a 5 l
  9. stirringthe whole stirred for 1 hour
  10. filtrationAfter filtration
  11. additionthe solution was poured into a Keller flask
  12. customprovided with a stirrer
  13. temperatureexternally cooled
  14. customlower than +5° C
  15. stirringAfter approximately 1 hour of stirring
  16. customthe product, thus separated
  17. filtrationwas filtered with a Buchner
  18. washwashed with water
  19. customThe raw product was crystallized many times from ligroin in the presence of animal charcoal

Sources & evidence

ORD record
ord-f1587fe15e5d4ce39941047018da03e6
Source dataset
uspto-grants-1985_05
Patent number
US04515888

Reaction notes

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