1-Ethyl-3-(3'-dimethylaminopropyl)carbodiimide → 2,3,5,6-tetrafluoro-4-methyl-N-(2-methylcyclohexyl)benzamide

HRID 339410

反応式

HRID 339410 の反応式
[F:1][C:2]1[C:7]([F:8])=[C:6]([C:9]([OH:11])=O)[C:5]([F:12])=[C:4]([F:13])[C:3]=1[CH3:14].C1C=CC2N(O)N=NC=2C=1.CCN=C=NCCCN(C)C.[CH3:36][CH:37]1[CH2:42][CH2:41][CH2:40][CH2:39][CH:38]1[NH2:43]>C(Cl)Cl.CN(C=O)C>[F:12][C:5]1[C:4]([F:13])=[C:3]([CH3:14])[C:2]([F:1])=[C:7]([F:8])[C:6]=1[C:9]([NH:43][CH:38]1[CH2:39][CH2:40][CH2:41][CH2:42][CH:37]1[CH3:36])=[O:11]

参加物

7

反応物 4

HCID 159081-Ethyl-3-(3'-dimethylaminopropyl)carbodiimideHCID 234322-MethylcyclohexylamineHCID 69548p-Toluic acid, 2,3,5,6-tetrafluoro-HCID 757711-Hydroxybenzotriazole

生成物 1

HCID 251295652,3,5,6-tetrafluoro-4-methyl-N-(2-methylcyclohexyl)benzamide収率 90%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

2,3,5,6-tetrafluoro-p-toluic acid (4.00 g, 19.22 mmol), HOBt (5.19 g, 38.44 mmol) and EDCI (4.42 g 23.06 mmol) were mixed in 200 ml of anhydrous DCM and 30 ml of anhydrous DMF. The mixture was cooled to 0° C. and allowed to stir under Ar for 15 minutes. To the mixture was added 2-methylcyclohexanamine (3.05 mL, 23.06 mmol) and the reaction mixture was allowed to slowly warm to ambient temperature and stirred overnight. The reaction mixture was diluted with DCM, washed with 1N HCl, water, aqueous NaHCO3, water and brine, drying over MgSO4, filtration and removal of solvent in vacuo, afforded the crude product as a pale yellow solid Recrystallization (EtOH/H2O) and drying in vacuo gave 5.23 g of the title compound as a white solid (mixture of 2 diasteromers, 90%). 1H NMR (CDCl3) δ 0.95, 1.01 (d, J=7.0, 6.6 Hz, 3H) 1.1-2.1 (m, 9H), 2.29 (m, 3H), 3.70, 4.29 (m, 1H), 5.65, 5.92 (m, 1H). MS (304.1, M+H). m. p. 202-204° C.

後処理

  1. temperatureto slowly warm to ambient temperature
  2. stirringstirred overnight
  3. washwashed with 1N HCl, water, aqueous NaHCO3, water and brine
  4. dry with materialdrying over MgSO4, filtration and removal of solvent in vacuo
  5. customafforded
  6. customthe crude product as a pale yellow solid Recrystallization (EtOH/H2O)
  7. customdrying in vacuo

出典と根拠

ORDレコード
ord-086c3649e49740e78a87023d7377d97e
出典データセット
uspto-grants-2014_11
特許番号
US08895050B2

関連ノート

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