Ethanol → HCID 54033689, compound
Reaction equation
[CH2:1]([OH:3])[CH3:2].[H-].[Na+].[C:6]([N:10]=[N:11][C:12]1([N:18]=[C:19]=[S:20])[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)([CH3:9])([CH3:8])[CH3:7].O>CCCCC>[C:6]([N:10]=[N:11][C:12]1([NH:18][C:19]([O:3][CH2:1][CH3:2])=[S:20])[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]1)([CH3:9])([CH3:7])[CH3:8]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 25 °C
Procedure
To 50 ml of ethanol 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 for 2 hours and then allowed to stand overnight. The next morning the reaction mixture was poured into 200 ml water and the product extracted with 50 ml pentane. The pentane extract was washed twice with water, once with 10% NaHCO3, dried over anhydrous Na2SO4, filtered and the pentane evaporated under reduced pressure to leave a mushy solid. The solid was slurried in a small amount of cold pentane and filtered. The solids were air dried and weighed 7.1 grams (52% crude yield) and melted at 57°-62° C. The product had a strong broad band at 1515 cm-1 and a sharp NH band at 3300 cm-1 in its infrared spectrum.
Workup
- waitto stand overnight
- extractionthe product extracted with 50 ml pentane
- extractionThe pentane extract
- washwas washed twice with water, once with 10% NaHCO3
- dry with materialdried over anhydrous Na2SO4
- filtrationfiltered
- customthe pentane evaporated under reduced pressure
- customto leave a mushy solid
- filtrationfiltered
- customdried
Sources & evidence
- ORD record
- ord-fb9ec48fce5c413a9fa9d024ea70651f
- Source dataset
- uspto-grants-1977_06
- Patent number
- US04028344
Reaction notes
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