1-(Isocyanatomethyl)-3-methoxybenzene → 3-(3-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

HRID 2098288ノート

反応式

HRID 2098288 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]=[C:8]=[O:9].[N+:13](=[C:15]1[N:19]=[CH:18][N:17]=[C:16]1[C:20]([NH2:22])=[O:21])=[N-:14]>CS(C)=O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:10]=[CH:11][CH:12]=1)[CH2:6][N:7]1[C:8](=[O:9])[N:19]2[CH:18]=[N:17][C:16]([C:20]([NH2:22])=[O:21])=[C:15]2[N:13]=[N:14]1

参加物

4

反応物 2

HCID 36446341-(Isocyanatomethyl)-3-methoxybenzeneHCID 534265854-Diazo-4H-imidazole-5-carboxamide

生成物 1

HCID 441283783-(3-Methoxybenzyl)-4-oxo-3,4-dihydroimidazo[5,1-d][1,2,3,5]tetrazine-8-carboxamide

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

実験手順

Meta-methoxybenzyl isocyanate (Sigma Aldrich) (0.390 g, 2.4 mmol) was added drop wise to a suspension of 5-diazoimidazole-4-carboxamide (0.274 g, 2 mmol) in dry dimethylsulfoxide (2.5 mL) at room temperature under nitrogen. The resulting mixture was stirred at room temperature overnight. The reaction was quenched by the addition of ice and the solid product (off-white) removed by filtration, washed with water and ethyl acetate, and recrystallised from chloroform. Yield: 0.335 g, 56%. IR vmax/cm−1 3092, 1730, 1678, 1601. 1H NMR δH (DMSO-d6) 3.76 (3H, s, Me), 5.49 (2H, s, CH2Ar), 6.89-6.92 (1H, m, ArH), 7.00-7.02 (1H, m, ArH), 7.28-7.32 (1H, s, ArH), 7.70 (1H, br s, NH), 7.82 (1H, br s, NH), 8.84 (1H, s, 6-H). δC (DMSO-d6) 52.2, 55.6, 113.7, 114.0, 120.4, 129.5, 130.1, 131.4, 134.9, 137.6, 139.7, 159.9, 162.0. Found 301.1091. Calc for (M+H): 301.1049. Found C, 51.3; H 3.9; N 27.8. Calc. for C13H12N6O3C, 52.0; H, 4.0; N, 28.0%.

後処理

  1. customThe reaction was quenched by the addition of ice
  2. customthe solid product (off-white) removed by filtration
  3. washwashed with water and ethyl acetate
  4. customrecrystallised from chloroform

出典と根拠

ORDレコード
ord-cdd16747ee244d7eaed8ddc9b311da1c
出典データセット
uspto-grants-2013_05
特許番号
US08450479B2

反応ノート

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