Ammonium Hydroxide → HCID 21250949, compound

HRID 1421288Notes

Reaction equation

HRID 1421288 reaction equation
[CH:1]1[CH:6]=[C:5]2[C:7]([N:9]([CH2:12][C:13]([OH:15])=O)[C:10](=[O:11])[C:4]2=[CH:3][CH:2]=1)=[O:8].C(N1[CH:27]=[CH:26]N=C1)(N1C=CN=C1)=O.[OH-].[NH4+:29]>O1CCCC1.O>[C:10]1(=[O:11])[N:9]([CH:12]([C:27]2[CH:26]=[CH:3][CH:2]=[CH:1][CH:6]=2)[C:13]([NH2:29])=[O:15])[C:7](=[O:8])[C:5]2=[CH:6][CH:1]=[CH:2][CH:3]=[C:4]12

Participants

6

Reactant 3

HCID 14923Ammonium HydroxideHCID 20825N-PhthaloylglycineHCID 682631,1'-Carbonyldiimidazole

Product 1

HCID 21250949HCID 21250949, compoundYield 76%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a stirred solution of N-phthaloylglycine (2.50 g, 8.89 mmol) in tetrahydrofuran (50 mL) is add ed carbonyldiimidazole (1.50 g, 9.25 mmol) and a few crystals of 4-NN-dimethylaminopyridine. The reaction is then heated to 50° C. for 45 minutes. After the reaction mixture had cooled 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 was filtered and the solid washed with copious amounts of water. The solid was dried in vacuo (60° C.,<1 mm) to afford 1.9 g (76%) of α-phthalimidophenyl-acetamide as an off-white powder: mp 218-220.C; H NMR (DMSO-d6)δ 9.00-7.75 (m, 4H, Ar), 7.61 (br s, 1H, CONH2), 7.55-7.20 (m, 6H, Ar, CONH2), 5.82 (s, 1H, 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.

Workup

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

Sources & evidence

ORD record
ord-8d63ca06d86645a1835e3ded40e9ba8c
Source dataset
uspto-grants-2000_06
Patent number
US06075041

Reaction notes

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