Methyl isothiocyanate → HCID 178481702, compound

HRID 858830Notes

Reaction equation

HRID 858830 reaction equation
[CH3:1][N:2]=[C:3]=[S:4].[N:5]1([CH2:11][CH2:12][C:13]([NH:15][NH2:16])=O)[CH2:10][CH2:9][O:8][CH2:7][CH2:6]1>CCO>[CH3:1][N:2]1[C:13]([CH2:12][CH2:11][N:5]2[CH2:6][CH2:7][O:8][CH2:9][CH2:10]2)=[N:15][N:16]=[C:3]1[SH:4]

Participants

4

Reactant 2

HCID 11167Methyl isothiocyanateHCID 16784403-(Morpholin-4-yl)propanehydrazide

Product 1

HCID 178481702HCID 178481702, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent2×

Procedure

Prepared according to a procedure reported for related compounds: Henichart, J. P. et al. J. Het Chem. 1977, 14, 615. Methyl isothiocyanate (9.08 g, 0.124 mol) in EtOH (50 mL) was added at room temperature to a stirred solution of 3-morpholin-4-ylpropanohydrazide (21.5 g, 0.124 mol) in EtOH (200 mL). The mixture was refluxed for 8 h, then removed from heat and stirred at room temperature for 16 h. The EtOh was removed under reduced pressure to give the crude material as a yellow oil. The oil was purified by column chromatography through silica gel, eluting with CH2Cl2/MeOH to afford the title compound. (6 g, 21.2%).

Workup

  1. customPrepared
  2. temperatureThe mixture was refluxed for 8 h
  3. customremoved
  4. temperaturefrom heat
  5. customThe EtOh was removed under reduced pressure
  6. customto give the crude material as a yellow oil
  7. customThe oil was purified by column chromatography through silica gel
  8. washeluting with CH2Cl2/MeOH

Sources & evidence

ORD record
ord-31d70e1d10f04e9b885924b96a1ac6bb
Source dataset
uspto-grants-2006_12
Patent number
US07148226B2

Reaction notes

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