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Ammonium Hydroxide → HCID 21250949、化合物

HRID 1451838
ノート
印刷プレビュー

反応式

HRID 1451838 の反応式
[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
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

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

生成物 1

HCID 21250949HCID 21250949、化合物収率 76%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
50 °C

実験手順

To a stirred solution of N-phthaloylglycine (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-N,N-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 2-phthalimido-2-phenylacetamide 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.

後処理

  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)

出典と根拠

ORDレコード
ord-aa137b7587484465905198debfb7f281
出典データセット
uspto-grants-1997_02
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05605914

反応ノート

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