Water → HCID 10774329、化合物

HRID 389079ノート

反応式

HRID 389079 の反応式
Cl[C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.[CH3:15][NH2:16].O.C(Cl)Cl.CO>CCO.ClCCl>[CH3:15][NH:16][C:2]1[C:3]2[N:4]([CH:12]=[CH:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

参加物

7

反応物 4

HCID 962WaterHCID 6329Methylamine2 回HCID 107745254-Chloroimidazo[1,2-a]quinoxalineHCID 21226129Dichloromethane methanol

生成物 1

HCID 10774329HCID 10774329、化合物収率 93%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 6344Dichloromethane溶媒

実験手順

Compound 12 (0.110 g, 0.54 mmol) is solubilized in EtOH (10 ml), and then a solution of methylamine in water (40% by weight) (0.15 ml, 1.74 mmol) is introduced. The mixture is left under stirring in an autoclave, at room temperature, for at least 15 h. The product, initially insoluble, is solubilized shortly thereafter. The progression of the reaction is controlled by TLC, eluent: CH2Cl2/MeOH (95/5). At the end of 15 h, 1.5 eq (0.06 ml) of methylamine are added. After 5 h of stirring, the reaction progresses no further. The solvent is evaporated dry under vacuum. The yellowish residue obtained is solubilized in dichloromethane (10 ml). This organic phase is washed using a saturated sodium bicarbonate solution (10 ml) and then water (10 ml). It is then dried on Na2SO4 and then evaporated under vacuum. A white solid is recovered. The residue is purified on a silica gel column in order to eliminate traces of the starting product, eluent: CH2Cl2/AcEt (70/30). A white solid (0.99 g, 93%) is obtained; 1H NMR (300 MHz, DMSO-d6) δ: 7.92 (s, 1H, C—CH—N), 7.75 (dd, J1=1.22 Hz, J2=8.17 Hz, 1H, ArH), 7.65 (dd, J1=1.26 Hz, J2=8.06 Hz, 1H, ArH), 7.52 (s, 1H, N—CH—C), 7.4 (t, 1H, ArH), 7.25 (t, 1H, ArH), 6.15 (s, 1H, NH), 3.25 (d, 3H, —CH3); 13C NMR (200 MHz, DMSO-d6) δ: 142.25, 139.17, 131.99, 129.40, 128.17, 127.20, 125.14, 124.34, 114.14, 113.89, 29.20. Analysis calculated for C11H10N4: C, 66.65; H, 5.08; N, 28.26. Experimental: C, 66.26; H, 5.53; N, 28.23.

後処理

  1. waitThe mixture is left
  2. stirringAfter 5 h of stirring
  3. customThe solvent is evaporated
  4. customdry under vacuum
  5. customThe yellowish residue obtained
  6. washThis organic phase is washed
  7. customIt is then dried on Na2SO4
  8. customevaporated under vacuum
  9. customA white solid is recovered
  10. customThe residue is purified on a silica gel column in order

出典と根拠

ORDレコード
ord-5ef19d6a98714b38891d1229685a333e
出典データセット
uspto-grants-2013_02
特許番号
US08378098B2

反応ノート

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