Sodium Carbonate → 2-Phthalimidoacetamide

HRID 2211247Notes

Reaction equation

HRID 2211247 reaction equation
Cl.[NH2:2][CH2:3][C:4]([NH2:6])=[O:5].C(=O)([O-])[O-].[Na+].[Na+].C(N1[C:22](=[O:23])[C:21]2=[CH:24][CH:25]=[CH:26][CH:27]=[C:20]2[C:19]1=[O:28])(OCC)=O>O.C(O)C>[CH:25]1[CH:24]=[C:21]2[C:22]([N:2]([CH2:3][C:4]([NH2:6])=[O:5])[C:19](=[O:28])[C:20]2=[CH:27][CH:26]=1)=[O:23]

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 31187N-CarbethoxyphthalimideHCID 2723639Glycinamide hydrochloride

Product 1

HCID 210532-PhthalimidoacetamideYield 65%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

To a stirred solution of glycinamide hydrochloride (2.20 g, 20.0 mmol) and sodium carbonate (2.54 g, 24 mmol) in 25 mL of water is added N-carbethoxyphthalimide (4.38 g, 20.0 mmol). The resulting suspension is stirred for 1.5 hour and then filtered to afford 3.22 g (79%) of crude product as a white powder. The crude product is slurried in 200 mL of refluxing ethanol and, after cooling to room temperature, the resulting suspension is filtered and the solid dried in vacuo (60° C., <1 mm) to afford 2.65 g (65%) of N-phthaloylglycinamide, which can be alternatively named as phthalimidoacetamide, as a white powder: mp 199°-201° C.; 1H NMR (dmso-d6) δ 8.00-7.8 (m, 4 H, Ar), 7.70 (br s, 1 H, CONH2), 7.26 (br s, 1 H, CONH2), 4.16 (s, 2 H, CH2); 13C NMR (dmso-d6) δ 167.8, 167.5, 134.4, 131.7, 123.1, 39.9. Anal. Calculated for C11H10N2O3. Theoretical: C, 60.55; H, 4.62; N, 12.84. Found: C, 60.49; H, 4.59; N, 12.82.

Workup

  1. filtrationfiltered
  2. customto afford 3.22 g (79%) of crude product as a white powder
  3. filtrationthe resulting suspension is filtered
  4. customthe solid dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-2737bafcff66478ab43dc27e4a3bc908
Source dataset
uspto-grants-1995_10
Patent number
US05463063

Reaction notes

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