Toluene → HCID 5853474, compound

HRID 1423966Notes

Reaction equation

HRID 1423966 reaction equation
S(Cl)(Cl)=[O:2].C(N[CH:9]([CH3:11])[CH3:10])(C)C.[CH:12]1([NH:18][CH:19]2[CH2:24][CH2:23][CH2:22][CH2:21][CH2:20]2)[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1.C[CH:26]1[CH2:30][CH2:29][CH2:28][O:27]1.[C:31]1([CH3:37])C=CC=C[CH:32]=1>O>[CH:19]1([N:18]([CH:12]2[CH2:13][CH2:14][CH2:15][CH2:16][CH2:17]2)[C:37](=[O:2])/[CH:31]=[CH:32]/[C:10]2[CH:9]=[CH:11][C:28]([O:27][CH3:26])=[CH:29][CH:30]=2)[CH2:20][CH2:21][CH2:22][CH2:23][CH2:24]1

Participants

7

Reactant 5

HCID 1140Toluene2×HCID 73012-MethyltetrahydrofuranHCID 7582DicyclohexylamineHCID 7912DiisopropylamineHCID 24386Thionyl Chloride

Product 1

HCID 5853474HCID 5853474, compoundYield 50%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

5.0 g (0.028 mol) of 3-methoxycinammic acid, 50 ml of toluene and 0.23 g (3.0 mmol) of N,N-dimethylormamide are provided and mixed with 4.01 g (0.034 mol) of thionyl chloride. Stirring is performed overnight. Then heating is performed to 50° C. and excess thionyl chloride and toluene are distilled off under vacuum. At normal pressure and 60° C. toluene and 4.0 g (0.031 mol) of diisopropylamine are added. Then a solution of 5.6 g (0.031 mol) of dicyclohexylamine in toluene is added. Stirring is performed for 30 minutes at 60° C. followed by cooling to RT. The reaction mixture is mixed with water and 2-methyltetrahydrofuran and heated to 70° C. Following phase separation the organic phase is washed twice with water, once with 1 N soda lye and further twice with water at 50° C. The organic phase is rotated and recrystallised from n-heptane. The crystallised solid is drawn off at 0° C., washed with n-heptane and dried, wherein the desired compound is obtained.

Workup

  1. temperatureThen heating
  2. customis performed to 50° C.
  3. distillationexcess thionyl chloride and toluene are distilled off under vacuum
  4. stirringStirring
  5. waitis performed for 30 minutes at 60° C.
  6. temperatureheated to 70° C
  7. customFollowing phase separation the organic phase
  8. washis washed twice with water, once with 1 N soda lye and further twice with water at 50° C
  9. customrecrystallised from n-heptane
  10. customis drawn off at 0° C.
  11. washwashed with n-heptane
  12. customdried

Sources & evidence

ORD record
ord-f106d950414c4119a62044c226d9fcfd
Source dataset
uspto-grants-2015_01
Patent number
US08927605B2

Reaction notes

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