HCID 4777624, compound → HCID 68956891, compound

HRID 1784929Notes

Reaction equation

HRID 1784929 reaction equation
[C:1]([O:12][CH3:13])(=[O:11])[C:2]1[CH:10]=[CH:9][CH:8]=[C:4]([C:5]([O-:7])=O)[CH:3]=1.[CH3:14][C:15]1[N:16]=[C:17]([CH2:20][NH:21][CH:22]([CH3:24])[CH3:23])[S:18][CH:19]=1>CCN(CC)CC.O=S(Cl)Cl.C(Cl)Cl>[CH:22]([N:21]([CH2:20][C:17]1[S:18][CH:19]=[C:15]([CH3:14])[N:16]=1)[C:5]([C:4]1[CH:3]=[C:2]([CH:10]=[CH:9][CH:8]=1)[C:1]([O:12][CH3:13])=[O:11])=[O:7])([CH3:24])[CH3:23]

Participants

6

Reactant 2

HCID 4777624HCID 4777624, compoundHCID 69512791,3-Benzenedicarboxylic acid, monomethyl ester

Product 1

HCID 68956891HCID 68956891, compoundYield 93%

Reagents, catalysts & solvents 3

HCID 8471TriethylamineCatalystHCID 6344DichloromethaneSolventHCID 24386Thionyl ChlorideSolvent

Conditions

Temperature
90 °C

Procedure

Et3N (1 drop, catalytic) was added to a stirred suspension of mono-Methyl isophthalate (0.294 mmol, 1.0 eq) in 2 ml SOCl2 under Ar. The mixture was heated to reflux at 90° C. for 2 h. The reaction was cooled to RT, and the solvent was removed in vacuo. The residue was placed under an Ar atmosphere and dissolved in 2 ml anh CH2Cl2. The resulting solution was treated with a solution of N-((4-methylthiazol-2-yl)methyl)propan-2-amine (0.294 mmol, 1.0 eq made from reductive amination of 4-methylthiazole-2-carbaldehyde with isopropylamine) dissolved in 1 ml anh CH2Cl2 under Ar. After stirring at RT for 30 min, the reaction was treated with ET3N (0.294 mmol, 1 eq). After stirring at RT for 30 min, the reaction is poured into a seperatory funnel, washed with sat. NaHCO3 (×1), water (×3), brine (×1), and dried over Na2SO4. The inorganics were removed via filtration, and the solvent was removed in vacuo yielding the crude product in 93% yield.

Workup

  1. temperatureThe mixture was heated
  2. temperatureThe reaction was cooled to RT
  3. customthe solvent was removed in vacuo
  4. dissolutiondissolved in 2 ml anh CH2Cl2
  5. additionthe reaction was treated with ET3N (0.294 mmol, 1 eq)
  6. stirringAfter stirring at RT for 30 min
  7. additionthe reaction is poured into a seperatory funnel
  8. washwashed with sat. NaHCO3 (×1), water (×3), brine (×1)
  9. dry with materialdried over Na2SO4
  10. customThe inorganics were removed via filtration
  11. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-470f26b5a4894efe91e8c20c998849a6
Source dataset
uspto-grants-2009_03
Patent number
US07504420B2

Reaction notes

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