Sec-Butylamine → HCID 23335972, compound

HRID 1112563Notes

Reaction equation

HRID 1112563 reaction equation
[Cl:1][C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[C:6](Cl)[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]=1[CH3:15].[CH:16]([NH2:20])([CH2:18][CH3:19])[CH3:17]>C1CCCCC1>[CH:16]([NH:20][C:6]1[C:5]([N+:12]([O-:14])=[O:13])=[CH:4][C:3]([CH3:15])=[C:2]([Cl:1])[C:7]=1[N+:8]([O-:10])=[O:9])([CH2:18][CH3:19])[CH3:17]

Participants

4

Reactant 2

HCID 24874Sec-ButylamineHCID 23335977HCID 23335977, compound

Product 1

HCID 23335972HCID 23335972, compound

Reagents, catalysts & solvents 1

HCID 8078CyclohexaneSolvent

Procedure

A mixture of 10.04 g. (0.04 mole) of 2,4-dichloro-3,5-dinitrotoluene, 5.85 g. (0.08 mole) of sec-butylamine and 200 ml. of cyclohexane is stirred at reflux for six hours. The mixture is filtered and the filtrate is evaporated at reduced pressure. The filtrate is partitioned between ether and dilute hydrochloric acid. The organic phase is washed with water and brine, dried over magnesium sulfate and evaporated in vacuo. Crystallization of the residue from ethanol gives 7.71 g. of orange crystals, m.p. 40°-46° C. Two recrystallizations from ethanol give the analytical sample, m.p. 45°-47° C. Analysis Calcd. for C11H14ClN3O4 : C, 45.92; H, 4.90; Cl, 12.32; N, 14.61. Found: C, 45.96; H, 4.97; Cl, 12.36; N, 14.78.

Workup

  1. additionA mixture of 10.04 g
  2. temperatureat reflux for six hours
  3. filtrationThe mixture is filtered
  4. customthe filtrate is evaporated at reduced pressure
  5. customThe filtrate is partitioned between ether and dilute hydrochloric acid
  6. washThe organic phase is washed with water and brine
  7. dry with materialdried over magnesium sulfate
  8. customevaporated in vacuo
  9. customCrystallization of the residue from ethanol
  10. customgives 7.71 g
  11. customTwo recrystallizations from ethanol
  12. customgive the analytical sample, m.p. 45°-47° C

Sources & evidence

ORD record
ord-081d0da012e74968975d5dba55311034
Source dataset
uspto-grants-1978_10
Patent number
US04123250

Reaction notes

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