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Ammonium Hydroxide → HCID 21250949, 화합물

HRID 1531851
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HRID 1531851 반응식
[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
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참가 물질

6

반응물 3

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

생성물 1

HCID 21250949HCID 21250949, 화합물수율 76%

시약·촉매·용매 2

HCID 962Water용매HCID 8028Tetrahydrofuran용매

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온도
50 °C

실험 절차

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 rnL 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-phthalimidophenylacetamide as an off-white powder: mp 218-220° C.; 1H NMR (DMSO-d6) δ9.00-7.75 (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) δ168.2, 167.1, 135.6, 134,5, 131.4, 129.4, 127.9, 127.7, 123.1, 56.3.

후처리

  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)

출처 및 근거

ORD 기록
ord-36e24f007187490d939c80b8d4749ca9
출처 데이터셋
uspto-grants-2001_03
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06200987B1

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