Sulfuric Acid → HCID 21567581, compound
Reaction equation
[C:1]([N:5]=[N:6][C:7]([C:14]#[N:15])([CH3:13])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:3])[CH3:2].[OH:16]S(O)(=O)=O>>[C:1]([N:5]=[N:6][C:7]([C:14](=[O:16])[NH2:15])([CH3:13])[CH2:8][CH2:9][C:10]([OH:12])=[O:11])([CH3:4])([CH3:2])[CH3:3]Participants
Procedure
To 20 ml of 95% H2SO4 cooled to -10°C in a 50 ml round bottom flask immersed in an ice-salt bath, was added 6.0 grams (0.0284 moles) of 4-t-butylazo-4-cyanovaleric acid (from Example X) in small portions over one-half hour holding the temperature at -10°C. After the addition was complete, the mixture was stirred for an additional 4 hours at -5° to -10°C. After 3 hours, the reaction mixture was poured into 75 ml of ice water and the product extracted with 50 ml of methylene chloride. The methylene chloride layer was washed with 100 ml of cold water, dried over anhydrous sodium sulfate, filtered and the methylene chloride evaporated under reduced pressure to leave 4.3 grams (66% yield) of a white-yellow solid. The solid was slurried in 50 ml of pentane, filtered and the filter cake air dried. The purified material had a melting point of 97° -102°C (dec.) and its infrared spectrum was in agreement with the structure of 4-t-butylazo-4-carbamylvaleric acid.
Workup
- customimmersed in an ice-salt bath
- customat -10°C
- additionAfter the addition
- waitAfter 3 hours
- extractionthe product extracted with 50 ml of methylene chloride
- washThe methylene chloride layer was washed with 100 ml of cold water
- dry with materialdried over anhydrous sodium sulfate
- filtrationfiltered
- customthe methylene chloride evaporated under reduced pressure
Sources & evidence
- ORD record
- ord-91344fed52904c19af18acff39801e8a
- Source dataset
- uspto-grants-1976_01
- Patent number
- US03931143
Reaction notes
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