Water → HCID 10176641、化合物

HRID 1058510ノート

反応式

HRID 1058510 の反応式
[N+:1]([C:4]1[CH:12]=[CH:11][C:10](F)=[CH:9][C:5]=1[C:6]([NH2:8])=[O:7])([O-:3])=[O:2].[NH:14]1[CH2:16][CH2:15]1.O>CS(C)=O>[N:14]1([C:10]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([CH:9]=2)[C:6]([NH2:8])=[O:7])[CH2:16][CH2:15]1

参加物

5

反応物 3

HCID 962WaterHCID 9033AziridineHCID 186681655-Fluoro-2-nitrobenzamide

生成物 1

HCID 10176641HCID 10176641、化合物収率 47%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
-5 °C

実験手順

A stirred solution of 2-nitro-5-fluorobenzamide (Orrin, Eur. Pat. Appl. 19,388; Chem. Abstr. 1981, 94, 156538h) (480 mg, 2.61 mmol) in dry DMSO (2 mL) was treated with aziridine (0.54 mL, 10.4 mmol) at room temperature under N2 for 48 h, then poured into cold water (50 mL). Prolonged cooling at −5° C. gave a crystalline product that was collected and filtered throuhg a column of silica gel in EtOAc to give 11 (256 mg, 47%), mp (EtOAc) 172-174° C. 1H NMR [(CD3)2SO] δ8.01 & 7.61 (2xs, 2H, CONH2), 7.93 (d, J=8.9 Hz, 1H, H-3), 7.17 (dd, J=8.8, 2.4 Hz, 1H, H-4), 7.09 (d, J=2.3 Hz, 1H-6), 2.24 (s, 4H, aziridine-H ). Anal. Calcd. for C9H9N3O3: 52.17;H, 4.38; N, 20.29 Found: C, 52.29;H, 4.27; N, 20.25%.

後処理

  1. customgave a crystalline product that
  2. customwas collected
  3. filtrationfiltered throuhg a column of silica gel in EtOAc

出典と根拠

ORDレコード
ord-7bf5a40287c8495e8e483c313c401ef3
出典データセット
uspto-grants-2003_02
特許番号
US06517836B1

反応ノート

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