N,N-Dimethylbenzylamine → Meptyldinocap

HRID 1042375Notes

Reaction equation

HRID 1042375 reaction equation
[N+:1]([C:4]1[CH:9]=[C:8]([N+:10]([O-:12])=[O:11])[CH:7]=[C:6]([CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])[C:5]=1[OH:21])([O-:3])=[O:2].C(N(C)C)C1C=CC=CC=1.[C:32](Cl)(=[O:36])/[CH:33]=[CH:34]/[CH3:35]>CCCCCCC>[C:32]([O:21][C:5]1[C:6]([CH:13]([CH3:20])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH3:19])=[CH:7][C:8]([N+:10]([O-:12])=[O:11])=[CH:9][C:4]=1[N+:1]([O-:3])=[O:2])(=[O:36])/[CH:33]=[CH:34]/[CH3:35]

Participants

5

Reactant 3

HCID 7681N,N-DimethylbenzylamineHCID 643131trans-Crotonyl chlorideHCID 30324472,4-Dinitro-6-(octan-2-yl)phenol

Product 1

HCID 5284389MeptyldinocapYield 91.2%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
20 °C

Procedure

2,4-Dinitro-6-(1-methylheptyl)phenol (98.5 percent pure) (252 gm) is dissolved in heptane (225 gm). Benzyldimethylamine (140.8 gm) is added dropwise over 40 minutes, keeping the temperature of the mixture below 40° C., and the mixture is stirred for 15 minutes. Crotonyl chloride (139 gm) is then added dropwise over 30 minutes, keeping the temperature below 60° C., and the mixture is stirred at 60° C. for 30 minutes and cooled to less than 50° C. The mixture is washed twice with water and then cooled to 20° C. The mixture is washed with a mixture of methanol and aqueous sodium hydroxide, with water and methanol, and finally with dilute hydrochloric acid. The organic layer is stripped at 70° C. under vacuum to remove heptane and leave 2,4-dinitro-6-(1-methylheptyl)phenyl crotonate (282.6 gm) as an orange/brown oil.

Workup

  1. customthe temperature of the mixture below 40° C.
  2. customthe temperature below 60° C.
  3. stirringthe mixture is stirred at 60° C. for 30 minutes
  4. temperaturecooled to less than 50° C
  5. washThe mixture is washed twice with water
  6. washThe mixture is washed with a mixture of methanol and aqueous sodium hydroxide, with water and methanol
  7. customis stripped at 70° C. under vacuum
  8. customto remove heptane

Sources & evidence

ORD record
ord-f52ebcd7f5f24ce083d0a4f9e8aa4ff7
Source dataset
uspto-grants-2013_10
Patent number
US08557866B2

Reaction notes

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