Phosphorus oxychloride → HCID 18537209, compound

HRID 2298600Notes

Reaction equation

HRID 2298600 reaction equation
[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12](=[O:23])[NH:13][CH2:14][C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.P(Cl)(Cl)(Cl)=O>CN(C=O)C>[CH3:1][S:2][C:3]1[S:7][C:6]([C:8]([O:10][CH3:11])=[O:9])=[CH:5][C:4]=1[C:12]1[O:23][C:15]([C:16]2[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=2)=[CH:14][N:13]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 18537044Methyl 5-(methylthio)-4-[[(2-oxo-2-phenylethyl)amino]carbonyl]-2-thiophenecarboxylate

Product 1

HCID 18537209HCID 18537209, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a cooled (0° C.) solution of 80.1 mg (0.229 mmol) of methyl 5-methylthio-4-[N-(2-oxo-2-phenylethyl)carbamoyl]thiophene-2-carboxylate (as prepared in the previous step) in 2 mL of anhyd DMF was added 26.7 μL (0.286 mmol) of phosphorus oxychloride. After stirring for 20 h at room temperature, the mixture was concentrated in vacuo. The resulting yellow solid was recrystallized twice from MeOH to afford the title compound as a beige powder (48.8 mg, 64%). 1H-NMR (300 MHz, DMSO-d6) δ8.26 (s, 1H), 7.88 (s, 1H), 7.86 (d, 2H, J=7 Hz), 7.51 (m, 2H), 7.40 (m, 1H), 3.86 (s, 3H), and 2.79 (s, 3H). Mass spectrum (MALDI-TOF, α-cyano-4-hydroxycinnamic acid matrix) calcd. for C16H13NO3S2: 332.0 (M+H). Found: 331.9.

Workup

  1. concentrationthe mixture was concentrated in vacuo
  2. customThe resulting yellow solid was recrystallized twice from MeOH

Sources & evidence

ORD record
ord-a87f979182ed44479c9288db036df2b6
Source dataset
uspto-grants-2002_12
Patent number
US06492403B1

Reaction notes

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