Methanol → HCID 54509599, compound

HRID 436770Notes

Reaction equation

HRID 436770 reaction equation
[CH3:1][OH:2].[H-].[Na+].[C:5]([N:9]=[N:10][C:11]1([N:17]=[C:18]=[S:19])[CH2:16][CH2:15][CH2:14][CH2:13][CH2:12]1)([CH3:8])([CH3:7])[CH3:6]>O>[C:5]([N:9]=[N:10][C:11]1([NH:17][C:18]([O:2][CH3:1])=[S:19])[CH2:12][CH2:13][CH2:14][CH2:15][CH2:16]1)([CH3:8])([CH3:6])[CH3:7]

Participants

5

Reactant 3

HCID 887MethanolHCID 24758Sodium hydrideHCID 214311441-t-Butylazo-1-isothiocyanatocyclohexane

Product 1

HCID 54509599HCID 54509599, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

To 50 ml of methanol in a 125 ml erlenmeyer flask stirred with a magnetic stirrer, was slowly added 2.1 grams (0.05 moles) of 57% sodium hydride. The reaction mixture was cooled back to 25° C. and 11.2 grams (0.05 moles) of 1-t-butylazo-1-isothiocyanatocyclohexane was added dropwise over 5 minutes. The reaction mixture was stirred 24 hours at room temperature, poured into 300 ml water and the product extracted with 100 ml pentane. The pentane extract was washed with water, 10% NaHCO3 solution, dried over anhydrous Na2SO4, filtered, and the pentane evaporated under reduced pressure to leave 9.2 grams of a mushy semi-solid. The semi-solid was slurried in cold pentane and filtered. The solids were dried and weighed 5.6 grams (43.5% crude yield) and melted at 79°-82° C. The infrared spectrum of the product had a strong broad band at 1530 cm-1 and a sharp NH band at 3250 cm-1.

Workup

  1. extractionthe product extracted with 100 ml pentane
  2. extractionThe pentane extract
  3. washwas washed with water, 10% NaHCO3 solution
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. customthe pentane evaporated under reduced pressure

Sources & evidence

ORD record
ord-442138905c244de1bad908d5ae30c18f
Source dataset
uspto-grants-1977_06
Patent number
US04028344

Reaction notes

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