N-Iodosuccinimide → 2-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409529ノート

反応式

HRID 2409529 の反応式
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:19])=[CH:18][N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].C1C(=O)N([I:27])C(=O)C1>C(Cl)Cl>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][C:17]([CH3:19])=[C:18]([I:27])[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

参加物

4

反応物 2

HCID 120273N-IodosuccinimideHCID 667171682-(3,4-Dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole

生成物 1

HCID 667169392-(3,4-Dimethoxy-phenyl)-5-iodo-6-methyl-imidazo[2,1-b][1,3,4]thiadiazole

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

2-(3,4-dimethoxyphenyl)-6-methylimidazo[2,1-b][1,3,4]thiadiazole (0.346 g, 1.257 mmol) was dissolved in DCM (4.2 mL), and NIS (0.283 mg, 1.257 mmol) was added. The reaction mixture was stirred at RT overnight, quenched with sat. aq. thiosulfate and extracted with DCM. The organic layers were combined and washed with sat. aq. NH4Cl, dried (MgSO4), filtered and concentrated. The residue was suspended in Et2O, and the solid was filtered off, washed with Et2O and dried in vacuo affording the desired product (brown solid (0.295 g, 58%). TLC (cyclohexane/EtOAc 1:1) Rf 0.46; HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.53 min, [M+H]+ m/z 402.0; 1H NMR (300 MHz, CDCl3) δ/ppm 7.37 (s, 1H), 7.32 (d, J=8.3, 1H), 6.86 (d, J=8.3, 1H), 3.91 (d, J=14.3, 6H), 2.31 (s, 3H).

後処理

  1. customquenched with sat. aq. thiosulfate
  2. extractionextracted with DCM
  3. washwashed with sat. aq. NH4Cl
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. filtrationthe solid was filtered off
  8. washwashed with Et2O
  9. customdried in vacuo

出典と根拠

ORDレコード
ord-4160baea027f4cb98e127b06f29bb18f
出典データセット
uspto-grants-2014_08
特許番号
US08815918B2

反応ノート

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