Ammonium Hydroxide → HCID 21250949, compound

HRID 1417361Notes

Reaction equation

HRID 1417361 reaction equation
[C:1]1(=[O:21])[N:5]([CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7](O)=[O:8])[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12.C(N1C=CN=C1)([N:24]1C=CN=C1)=O.[OH-].[NH4+]>O1CCCC1.CN(C)C1C=CN=CC=1.O>[C:1]1(=[O:21])[N:5]([CH:6]([C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:7]([NH2:24])=[O:8])[C:4](=[O:16])[C:3]2=[CH:17][CH:18]=[CH:19][CH:20]=[C:2]12

Participants

7

Reactant 3

HCID 14923Ammonium HydroxideHCID 682631,1'-CarbonyldiimidazoleHCID 272803(1,3-Dioxo-1,3-dihydro-2H-isoindol-2-yl)(phenyl)acetic acid

Product 1

HCID 21250949HCID 21250949, compoundYield 76.3%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred mixture of α-phthalimidophenylacetic acid (2.50 g, 8.89 mmoL) in tetrahydrofuran (50 mL) is added carbonyldiimidazole (1.50 g, 9.25 mmoL) and a few crystals of 4-dimethylaminopyridine. The reaction is then heated to 50° C. for 45 minutes. After the reaction mixture cools to room temperature, 1 mL of concentrated ammonium hydroxide is added via syringe. The reaction is stirred for 1 hour, then diluted with 50 mL of water and partially concentrated to remove the majority of the tetrahydrofuran. The resulting slurry is filtered and the solid washed with copious amounts of water. The solid is dried in vacuo (60° C., <1 mm) to afford 1.9 g (76%) of α-phthalimidophenylacetamide, which may be alternatively named as N-phthaloylphenylglycinamide, as an off-white powder: mp 218°-220° C.; 1H NMR (DMSO-d6) δ 9.00-7.75 (m, 4 H, Ar), 7.61 (br s, 1 H, CONH2), 7.55-7.20 (m, 6 H, Ar, CONH2), 5.82 (s, 1 H, CHCO2); 13C NMR (DMSO-d6) δ 168.2, 167.1, 135.6, 134.5, 131.4, 129.4, 127.9, 127.7, 123.1, 56.3. Anal (C16H12N2O3), C, H, N.

Workup

  1. customcools to room temperature
  2. concentrationpartially concentrated
  3. customto remove the majority of the tetrahydrofuran
  4. filtrationThe resulting slurry is filtered
  5. washthe solid washed with copious amounts of water
  6. customThe solid is dried in vacuo (60° C., <1 mm)

Sources & evidence

ORD record
ord-4894897b50d34441b89ff641eecc7697
Source dataset
uspto-grants-1999_03
Patent number
US05877200

Reaction notes

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