Acetone → 4-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide

HRID 515798ノート

反応式

HRID 515798 の反応式
[NH2:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1.[Si]([C:17]#[N:18])(C)(C)C.[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[CH3:31][C:32]([CH3:34])=O>C(Cl)Cl>[C:17]([C:32]([NH:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([NH:8][CH3:9])=[O:7])=[C:4]([F:12])[CH:3]=1)([CH3:34])[CH3:31])#[N:18]

参加物

6

反応物 4

HCID 180AcetoneHCID 65367Trimethylsilyl triflateHCID 82115Trimethylsilyl cyanideHCID 441395214-Amino-2-fluoro-N-methylbenzamide

生成物 1

HCID 592965474-[(2-Cyanopropan-2-yl)amino]-2-fluoro-N-methylbenzamide収率 40%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

A mixture of 4-amino-2-fluoro-N-methylbenzamide (2 g, 11.9 mmol), TMSCN (2.2 mL, 17.9 mmol), TMSOTf (0.1 mL, 0.6 mmol), and acetone (10 mL, 140 mmol) in DCM (20 mL) was stirred at room temperature overnight. The white solid was filtered, washed with a small amount of DCM, and dried to afford 1.12 g of 4-((2-cyanopropan-2-yl)amino)-2-fluoro-N-methylbenzamide as a white solid. 1H NMR (300 MHz, DMSO-d6) δ 7.79 (t, 1H), 7.56 (t, 1H), 6.88 (s, 1H), 6.67 (dd, 1H), 6.54 (dd, 1H), 2.75 (d, 3H), 1.67 (s, 6H).

後処理

  1. filtrationThe white solid was filtered
  2. washwashed with a small amount of DCM
  3. customdried

出典と根拠

ORDレコード
ord-d9cc09fa78ed43669f81b39b6b08c6bf
出典データセット
uspto-grants-2015_08
特許番号
US09108944B2

反応ノート

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