Dimethylformamide → HCID 19939348, compound

HRID 35901Notes

Reaction equation

HRID 35901 reaction equation
[C:1]([C:4]1[CH:9]=[CH:8][C:7]([C:10]#[C:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])=[CH:6][CH:5]=1)([OH:3])=[O:2].C(=O)(O)[O-].[Na+].CN(C)C=O.I[CH2:32][CH3:33]>O>[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:10]#[C:11][C:12]([NH:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=2)=[O:13])=[CH:8][CH:9]=1)([O:3][CH2:32][CH3:33])=[O:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 6340IodoethaneHCID 516892Sodium BicarbonateHCID 19939340HCID 19939340, compound

Product 1

HCID 19939348HCID 19939348, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 1.00 g (3.77 mmol)3 -(4-carboxyphenyl)-N-phenylpropiolamide, 1.00 g (excess) anhydrous sodium bicarbonate and 25 mL dry N,N-dimethylformamide was stirred at room temperature. Added was 1.95 g (excess) iodoethane and the mixture heated at 70°-80° C. for 3 hrs. The mixture was allowed to cool to room temperature and poured into 75 mL water. The resulting solid was filtered and recrystallized from ethanol/water to provide 0.99 g (3.37 mmol, 90%)3-(4-carbethoxyphenyl)-N-phenylpropiolamide as a pale, yellow powder, mp=114°-115° C. NMR (CDCl3 /TMS): 1.40 (t, 3H), 4.39 (q, 2H), 7.16 (t, 1H), 7.36 (t, 2H), 7.60 (d, 4H), 7.90 (s, 1H), 8.03 (d, 2H)). IR (KBr): 3292, 2210, 1692, 1660. High resolution mass spectrum: Calculated; 294.113019. Measured; 294.112376.

Workup

  1. additionAdded
  2. temperaturethe mixture heated at 70°-80° C. for 3 hrs
  3. temperatureto cool to room temperature
  4. filtrationThe resulting solid was filtered
  5. customrecrystallized from ethanol/water

Sources & evidence

ORD record
ord-caa5fbc3b70d4daf8b055a25bf133994
Source dataset
uspto-grants-1995_05
Patent number
US05411977

Reaction notes

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