1-Methyl-4-nitro-1H-imidazole-2-carbonyl chloride → HCID 19108632, 화합물

HRID 327425노트

반응식

HRID 327425 반응식
[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]

참가 물질

5

반응물 2

HCID 191086291-Methyl-4-nitro-1H-imidazole-2-carbonyl chlorideHCID 19108657HCID 19108657, 화합물

생성물 1

HCID 19108632HCID 19108632, 화합물수율 68.8%

시약·촉매·용매 2

HCID 6344Dichloromethane용매HCID 8028Tetrahydrofuran용매

반응 조건

온도
-20 °C

실험 절차

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).

후처리

  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.)

출처 및 근거

ORD 기록
ord-144a0aa00bbe4581a4783800f13bf03a
출처 데이터셋
uspto-grants-1993_12
특허 번호
US05273991

반응 노트

불러오는 중…