Ethyl Acetate → BM 11

HRID 373791Notes

Reaction equation

HRID 373791 reaction equation
[OH-].[Na+].[CH:3]1([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[S:17]([NH2:20])(=[O:19])=[O:18])[CH2:9][CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[CH:21]1([N:27]=[C:28]=[S:29])[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]1.C(OCC)(=O)C>O.O.CC(C)=O.C(N(CC)CC)C.CO>[CH:3]1([NH:10][C:11]2[CH:16]=[CH:15][N:14]=[CH:13][C:12]=2[S:17]([NH:20][C:28]([NH:27][CH:21]2[CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)=[S:29])(=[O:19])=[O:18])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9]1

Participants

9

Reactant 4

HCID 8857Ethyl AcetateHCID 14289Cyclohexyl isothiocyanateHCID 14798Sodium HydroxideHCID 15135616HCID 15135616, compound

Product 1

HCID 3036083BM 11Yield 50%

Reagents, catalysts & solvents 4

HCID 887MethanolSolventHCID 962WaterSolventHCID 8471TriethylamineSolventHCID 18366337Propan-2-one--water (1/1)Solvent

Procedure

0.01 mol of NaOH dissolved in a minimum of water is added to a solution of 0.01 mol of (4-(cycloheptylamino)pyrid-3-yl)sulfonamide in 80 ml of a water/acetone mixture (1:1). The mixture is stirred with a magnetic rod, and 0.015 mol of cyclohexylisothiocyanate is added. Stirring is continued, while the reaction is followed by TLC (silica gel 60F254; mobile phase: ethyl acetate 9, methanol 1, triethylamine 0.2). Gentle heating can accelerate the reaction. The mixture is evaporated under reduced pressure and the residue is taken up in 100 ml of 0.2N NaOH. Any insoluble material is filtered out and the solution is corrected to pH 6.5-7 and left to crystallize for 1 hour in the refrigerator. The precipitate collected is suspended in 100 ml of a water/acetone mixture (4:1) saturated with NaHCO3. The mixture is stirred for 1 hour and then filtered, and the filtrate, brought back to pH 6.5-7, is left to crystallize in the refrigerator. The crystals are collected, washed in cold water and dried under vacuum at normal temperature. Yield is around 50-60%. Melting point: 195°-197° C.

Workup

  1. additionis added
  2. temperatureGentle heating can
  3. customthe reaction
  4. customThe mixture is evaporated under reduced pressure
  5. filtrationAny insoluble material is filtered out
  6. waitleft
  7. customto crystallize for 1 hour in the refrigerator
  8. customThe precipitate collected
  9. stirringThe mixture is stirred for 1 hour
  10. filtrationfiltered
  11. waitis left
  12. customto crystallize in the refrigerator
  13. customThe crystals are collected
  14. washwashed in cold water
  15. customdried under vacuum at normal temperature

Sources & evidence

ORD record
ord-c109f0f0a3b64d8fbc4956c62e237afc
Source dataset
uspto-grants-1992_11
Patent number
US05166162

Reaction notes

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