Triethylamine → HCID 69642450, compound

HRID 11430Notes

Reaction equation

HRID 11430 reaction equation
[S:1]1[C:5]([C:6]([O-:8])=O)=[CH:4][CH:3]=[C:2]1[C:9]([O:11][CH3:12])=[O:10].S(Cl)(Cl)=O.[C:17]1([CH3:26])[CH:22]=[CH:21][C:20]([C@@H:23]([NH2:25])[CH3:24])=[CH:19][CH:18]=1.C(N(CC)CC)C>C(Cl)Cl.CN(C=O)C>[CH3:12][O:11][C:9]([C:2]1[S:1][C:5]([C:6](=[O:8])[NH:25][C@H:23]([C:20]2[CH:21]=[CH:22][C:17]([CH3:26])=[CH:18][CH:19]=2)[CH3:24])=[CH:4][CH:3]=1)=[O:10]

Participants

7

Reactant 4

HCID 8471TriethylamineHCID 24386Thionyl ChlorideHCID 6946556HCID 6946556, compoundHCID 7015759(S)-1-(p-tolyl)ethanamine

Product 1

HCID 69642450HCID 69642450, compoundYield 71%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Conditions

Temperature
80 °C

Procedure

A solution of 1.4 g (7.5 mmol) of methyl thiophen-2,5-dicarboxylate in CH2Cl2 (5 ml) is treated with 1.5 ml (18 mmol) thionylchloride and one drop of DMF and subsequently heated at 80° C. for 1 hour. The solvent and excess of thionylchloride are evaporated under reduced pressure, and the residue is dissolved in CH2Cl2 (10 ml) and treated slowly with (S)-1-(p-tolyl)ethylamine (1.0 g, 7.4 mmol) in CH2Cl2 (10 ml) and triethylamin (2 ml, 14.2 mmol). Stirring at rt is continued for 1 additional hour. The product is isolated after acidic work-up and recrystallisation as yellow solid (mp=165° C.) in 71% yield (1.6 g).

Workup

  1. customThe solvent and excess of thionylchloride are evaporated under reduced pressure
  2. dissolutionthe residue is dissolved in CH2Cl2 (10 ml)
  3. customThe product is isolated
  4. customafter acidic work-up and recrystallisation as yellow solid (mp=165° C.) in 71% yield (1.6 g)

Sources & evidence

ORD record
ord-ec579a0bb64c4ff396c5f146d1122968
Source dataset
uspto-grants-2006_08
Patent number
US07098241B2

Reaction notes

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