Toluene → AC1NPBSN

HRID 399591Notes

Reaction equation

HRID 399591 reaction equation
[CH2:1]([N:8]([C:20](=[O:24])[CH2:21][C:22]#[N:23])[C:9]([NH:11][C:12]1[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[OH-].[Na+].C(OCC)(=O)C.C1(C)C=CC=CC=1>C(O)C.O>[NH2:23][C:22]1[N:11]([C:12]2[CH:17]=[CH:16][CH:15]=[C:14]([S:18][CH3:19])[CH:13]=2)[C:9](=[O:10])[N:8]([CH2:1][C:2]2[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=2)[C:20](=[O:24])[CH:21]=1

Participants

7

Reactant 4

HCID 1140TolueneHCID 8857Ethyl AcetateHCID 14798Sodium HydroxideHCID 2822824HCID 2822824, compound

Product 1

HCID 5201471AC1NPBSN

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

1-Benzyl-1-(cyanoacetyl)-3-[3-(methylthio)phenyl]urea (14.9 g) was suspended in ethanol (150 ml) and to this was added a solution of sodium hydroxide (2.34 g) in water (30 ml). This was stirred for 1 h then allowed to stand overnight at room temperature. The mixture was filtered to remove a dark impurity and the filtrate carbon treated. This solution was then evaporated to remove ethanol then diluted with water. It was extracted with ethyl acetate (150 ml) and the extracts washed with water (2×75 ml) then dried and evaporated to give a foam. This was taken up in a 1:1 mixture of ethyl acetate and toluene (100 ml). After standing for 1 h the product had precipitated. It was filtered off and washed with 1:1 toluene/hexane (50 ml) then dried to constant weight. Yield=9.06 g.

Workup

  1. waitto stand overnight at room temperature
  2. filtrationThe mixture was filtered
  3. customto remove a dark impurity
  4. additionthe filtrate carbon treated
  5. customThis solution was then evaporated
  6. customto remove ethanol
  7. additionthen diluted with water
  8. extractionIt was extracted with ethyl acetate (150 ml)
  9. washthe extracts washed with water (2×75 ml)
  10. customthen dried
  11. customevaporated
  12. customto give a foam
  13. waitAfter standing for 1 h
  14. customthe product had precipitated
  15. filtrationIt was filtered off
  16. washwashed with 1:1 toluene/hexane (50 ml)
  17. customthen dried to constant weight

Sources & evidence

ORD record
ord-27af93c379c040308eb8f82e5514c65b
Source dataset
uspto-grants-1998_10
Patent number
US05821366

Reaction notes

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