Ethyl Acetate → HCID 25235945、化合物

HRID 1360748

反応式

HRID 1360748 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]([NH:20][NH2:21])=[O:19])[CH:15]=[CH:14][C:12]=2[N:13]=1.[C:22]1([CH3:31])[CH:27]=[CH:26][CH:25]=[C:24]([N:28]=[C:29]=S)[CH:23]=1.CCN=C=NCCCN(C)C.CCOC(C)=O>CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([Cl:8])[C:3]=1[C:9]1[NH:10][C:11]2[CH:17]=[C:16]([C:18]3[O:19][C:29]([NH:28][C:24]4[CH:23]=[C:22]([CH3:31])[CH:27]=[CH:26][CH:25]=4)=[N:21][N:20]=3)[CH:15]=[CH:14][C:12]=2[N:13]=1

参加物

6

反応物 4

HCID 8857Ethyl AcetateHCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 69304m-TolylisothiocyanateHCID 577865852-(2,6-Dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide

生成物 1

HCID 25235945HCID 25235945、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 2-(2,6-dichloro-phenyl)-3H-benzoimidazole-5-carboxylic acid hydrazide (150 mg, 0.466 mmol) in DMF (3 mL) add m-tolyl isothiocyanate (69 uL, 0.512 mmol) and stir for 3.5 hr. Add EDCI (179 mg, 0.932 mmol) and heat to 80° C. for 1 hr. Upon cooling to room temp dilute the reaction with EtOAc (75 mL) and extract with water (15 mL). Evaporate the organic phase and recrystallize from toluene/EtOAc. Suspend the solid in 1 N NaOH. Collect the solid wash with water and Et2O to afford the title compound as a white solid: 1H NMR (400 MHz, MeOD) δ ppm 2.38 (s, 3H) 6.90 (d, J=7.58 Hz, 1H) 7.26 (t, J=7.77 Hz, 1H) 7.37 (d, J=1.77 Hz, 1H) 7.43 (s, 1H) 7.56-7.65 (m, 3H) 7.82 (d, J=8.59 Hz, 1H) 8.01 (dd, J=8.53, 1.33 Hz, 1H) 8.27 (s, 1H); MS m/z=436.1 (M+1).

後処理

  1. additiondilute
  2. extractionextract with water (15 mL)
  3. customEvaporate the organic phase
  4. customrecrystallize from toluene/EtOAc
  5. customCollect the solid
  6. washwash with water and Et2O

出典と根拠

ORDレコード
ord-bca6167e50be4eaa9b3112c60c0f3292
出典データセット
uspto-grants-2011_02
特許番号
US07879850B2

関連ノート

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