Sodium Carbonate → HCID 68542335, compound

HRID 1432122Notes

Reaction equation

HRID 1432122 reaction equation
[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([C:7]([OH:9])=O)[CH:5]=1.O=S(Cl)Cl.C([O-])([O-])=O.[Na+].[Na+].Cl.[CH2:28]([NH:31][CH2:32][CH3:33])[CH:29]=[CH2:30]>CN(C=O)C.C(Cl)Cl.C1(C)C=CC=CC=1>[CH3:1][O:2][C:3](=[O:16])[C:4]1[CH:12]=[C:11]([O:13][CH2:14][CH3:15])[CH:10]=[C:6]([C:7]([N:31]([CH2:28][CH:29]=[CH2:30])[CH2:32][CH3:33])=[O:9])[CH:5]=1

Participants

8

Reactant 4

HCID 10340Sodium CarbonateHCID 24386Thionyl ChlorideHCID 20193693N-Ethylprop-2-en-1-amine--hydrogen chloride (1/1)HCID 69357330HCID 69357330, compound

Product 1

HCID 68542335HCID 68542335, compound

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideCatalystHCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
80 °C

Procedure

A solution of 1.0 g (4.45 mmol) 5-ethoxy-isophthalic acid mono methyl ester, 10 ml toluene and 0.5 ml SOCl2 is treated with one drop DMF and heated to 80° C. till the evolution of gas ceases. After cooling down the mixture is evaporated, dissolved in 5 ml DCM and added to an at 0° C. stirred mixture of 10 ml 10% aqueous Na2CO3, 0.81 g (6.7 mmol) allyl ethyl amine hydrochloride (see IVb) and 5 ml DCM. After 1 h the layers are separated and the organic layer is washed with 1N HCl, brine, dried with sodium sulfate and evaporated to yield the N-allyl-5-ethoxy-N-ethyl-isophthalamic acid methyl ester. This ester is dissolved in 20 ml MeOH, treated with 15 ml 1N NaOH and stirred for 18 h. The methanol is evaporated, the residue acidified with 1N HCl and extracted with TBME. The organic layer is dried with sodium sulfate and evaporated to yield the title compound.

Workup

  1. temperatureAfter cooling down the mixture
  2. customis evaporated
  3. dissolutiondissolved in 5 ml DCM
  4. additionadded to an at 0° C.
  5. customAfter 1 h the layers are separated
  6. washthe organic layer is washed with 1N HCl, brine
  7. dry with materialdried with sodium sulfate
  8. customevaporated

Sources & evidence

ORD record
ord-e7476d40055c46dc99ac3b0978a76023
Source dataset
uspto-grants-2009_11
Patent number
US07612055B2

Reaction notes

Loading…