1-Methyl-4-nitro-1H-imidazole-2-carbonyl chloride → HCID 19108632、化合物

HRID 327425ノート

反応式

HRID 327425 の反応式
[CH3:1][N:2]([NH:4][C:5]([C:7]1[N:8]([CH3:13])[CH:9]=[C:10]([NH2:12])[N:11]=1)=[O:6])[CH3:3].[CH3:14][N:15]1[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=[C:16]1[C:23](Cl)=[O:24]>C1COCC1.C(Cl)Cl>[CH3:3][N:2]([NH:4][C:5]([C:7]1[N:8]([CH3:13])[CH:9]=[C:10]([NH:12][C:23]([C:16]2[N:15]([CH3:14])[CH:19]=[C:18]([N+:20]([O-:22])=[O:21])[N:17]=2)=[O:24])[N:11]=1)=[O:6])[CH3:1]

参加物

5

反応物 2

HCID 191086291-Methyl-4-nitro-1H-imidazole-2-carbonyl chlorideHCID 19108657HCID 19108657、化合物

生成物 1

HCID 19108632HCID 19108632、化合物収率 68.8%

試薬・触媒・溶媒 2

HCID 6344Dichloromethane溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-20 °C

実験手順

The amine from above was dissolved in dry THF (20 mL) and cooled to -20° C. The stirring reaction mixture was placed under argon and a solution of 1-methyl-4-nitroimidazole-2-carbonyl chloride (2.18 g, 11.5 mmol) in dry CH2Cl2 (10 mL) was added dropwise. The reaction was allowed to warm to room temperature and stirred overnight then concentrated to dryness and water was added. The suspension was filtered and the solid was washed with carbon tetrachloride and water, then dried in-vacuo (80° C.) to provide N-(N',N'-dimethylamino)-1-methyl-4-[1-methyl-4-nitroimidazole-2-carboxamido]imidazole-2-carboxamide as a pale yellow crystalline solid, 2.18 g (68.8% yield). A sample for analysis was obtained by recrystallization from water: mp 239° C. (dec.). TLC (5% MeOH/CHCl3) Rf 0.66. 1H--NMR (CDCl3); δ2.69 (s, 6H, N(CH3)2), 4.07 (s, 3H, N--CH3), 4.21 (s, 3H, N--CH3), 7.43 (s, 1H, NH). IR (nujol: υ3397 and 1678 cm-1. MS(El) m/z (rel. intensity) 336 (M+, 100), 293 (M+1-N(CH3)2, 85).

後処理

  1. customThe stirring reaction mixture
  2. temperatureto warm to room temperature
  3. concentrationthen concentrated to dryness and water
  4. additionwas added
  5. filtrationThe suspension was filtered
  6. washthe solid was washed with carbon tetrachloride and water
  7. customdried in-vacuo (80° C.)

出典と根拠

ORDレコード
ord-144a0aa00bbe4581a4783800f13bf03a
出典データセット
uspto-grants-1993_12
特許番号
US05273991

反応ノート

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