Thiophenol → HCID 86628936, compound

HRID 1176720Notes

Reaction equation

HRID 1176720 reaction equation
C1(S)C=CC=CC=1.[OH-].[K+].[CH2:10]([N:12]([C@H:25]1[CH2:30][C@H:29]([CH3:31])[S:28][C:27]2[S:32][CH:33]=[CH:34][C:26]1=2)S(C1C=CC=CC=1[N+]([O-])=O)(=O)=O)[CH3:11]>C(#N)C.O>[CH2:10]([NH:12][C@H:25]1[CH2:30][C@H:29]([CH3:31])[S:28][C:27]2[S:32][CH:33]=[CH:34][C:26]1=2)[CH3:11]

Participants

6

Reactant 3

HCID 7969ThiophenolHCID 14797Potassium HydroxideHCID 11538553HCID 11538553, compound

Product 1

HCID 86628936HCID 86628936, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
5 °C

Procedure

Benzenethiol (3.2 mL) is dissolved in acetonitrile (15 mL). It is cooled under 5° C. and a mixture of potassium hydroxide (1.73 g) in water (4.2 mL) is added, maintaining the temperature under 10° C. The temperature is allowed to rise to 20-25° C. and a solution of trans-4-[N-ethyl-N-(2-nitrobenzenesulfonyl)amino]-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran (4.9 g) in acetonitrile (10 mL) is added. The resulting mixture is heated at 50° C. and is maintained until completing the transformation. Water (80 mL) is added and it is vacuum distilled until the volatiles are removed. It is extracted with ethyl acetate (80 mL). The resulting organic phase is vacuum distilled to dryness and the obtained residue is chromatographed in a column (methylene chloride/methanol 94/6), obtaining 1.9 g of trans-4-(N-ethylamino)-5,6-dihydro-6-methyl-4-H-thieno-[2,3-b]-thiopyran.

Workup

  1. additionis added
  2. temperaturemaintaining the temperature under 10° C
  3. customto rise to 20-25° C.
  4. temperatureThe resulting mixture is heated at 50° C.
  5. temperatureis maintained
  6. distillationdistilled until the volatiles
  7. customare removed
  8. extractionIt is extracted with ethyl acetate (80 mL)
  9. distillationdistilled to dryness
  10. customthe obtained residue is chromatographed in a column (methylene chloride/methanol 94/6)

Sources & evidence

ORD record
ord-cb812e2599b24d1bb91ca3023b9bdafc
Source dataset
uspto-grants-2010_11
Patent number
US07842821B2

Reaction notes

Loading…