Chlorine → 55296-29-2

HRID 1578573Notes

Reaction equation

HRID 1578573 reaction equation
[C:1]([NH:6][N:7]=[C:8]([CH3:18])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2].[Cl:19]Cl>CCCCC>[C:1]([N:6]=[N:7][C:8]([Cl:19])([CH3:18])[CH2:9][CH2:10][C:11]([O:13][CH2:14][CH2:15][CH2:16][CH3:17])=[O:12])([CH2:4][CH3:5])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 24526Chlorine2×HCID 71364225Butyl 4-[2-(2-methylbutan-2-yl)hydrazinylidene]pentanoate

Product 1

HCID 2141274555296-29-2Yield 104%

Reagents, catalysts & solvents 1

HCID 8003PentaneSolvent

Conditions

Temperature
-20 °C

Procedure

To a solution of 90 grams (.316 moles) of butyl levulinate t-amylhydrazone in 150 mls. of pentane in a 500 ml. round bottom flask was passed 10.9 grams (.154 moles) of chlorine holding the temperature at -20°C with a dry ice- isopropanol bath. The chlorine was added over 30 minutes and then the reaction was stirred an additional 15 minutes at -20°C and filtered. The filtrate was dried and the pentane evaporated leaving 46.6 grams of crude butyl 4-t-amylazo-4-chlorovalerate.

Workup

  1. customround bottom flask was passed
  2. customat -20°C
  3. filtrationfiltered
  4. customThe filtrate was dried
  5. customthe pentane evaporated

Sources & evidence

ORD record
ord-c12e4bf439e64c53903690e4b8d1536e
Source dataset
uspto-grants-1976_02
Patent number
US03937761

Reaction notes

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