2-Aminothiazole → N'-(2-Thiazolyl)-N-methyl-N-phenylformamidine

HRID 5149

反応式

HRID 5149 の反応式
[CH3:1][N:2]([CH:9]=O)[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.P(Cl)(Cl)(Cl)=O.[NH2:16][C:17]1[S:18][CH:19]=[CH:20][N:21]=1>C1(C)C=CC=CC=1.NC1SC=CN=1>[S:18]1[CH:19]=[CH:20][N:21]=[C:17]1[N:16]=[CH:9][N:2]([CH3:1])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1

参加物

6

反応物 3

HCID 21552-AminothiazoleHCID 24813Phosphorus oxychlorideHCID 66737N-Methylformanilide

生成物 1

HCID 53775884N'-(2-Thiazolyl)-N-methyl-N-phenylformamidine収率 94.2%

試薬・触媒・溶媒 2

HCID 21552-Aminothiazole触媒HCID 1140Toluene溶媒2 回

実験手順

To a stirred suspension of N-methylformanilide (67.6 g; 0.50 mole), toluene (25 g) and 2-aminothiazole (2.0 g; 0.02 mole) was added phosphorus oxychloride (45.8 mL; 0.50 mole) over 15 minutes. The temperature was maintained below 45° C. during this addition. Stirring was continued for 10 minutes, after which time a hot solution of 2-aminothiazole (48.0 g; 0.48 mole) in toluene (250 g) was added at 60°-65° C. over 45 minutes. The reaction was allowed to cool to room temperature with stirring and was quenched by dropwise addition into a mixture of 30% sodium hydroxide (325 g) and ice (300 g). The organic phase was washed with a mixture of water (100 g), sodium chloride (10 g), and sodium bicarbonate (7.5 g), followed by a saturated solution of sodium chloride (125 g); the resultant organic layer was dried over anhydrous magnesium sulfate, filtered, and concentrated to yield 98.3 g of crude product. Vacuum distillation gave pure 1 (60.0 g; 55.3%) as a yellow oil: bp 177° C. @ 0.5 mm Hg. 1H-NMR (CDCl3) 8.72 (s, 1H), 7.4-6.9 (m, 7H), 3.50 (S, 3H); IR(neat) 3075, 2950, 1615, 1580, 1490, 1345, 1310, 1120; MS (m/e) 217 (M+, base).

後処理

  1. temperatureThe temperature was maintained below 45° C. during this addition
  2. stirringwith stirring
  3. customwas quenched by dropwise addition into a mixture of 30% sodium hydroxide (325 g) and ice (300 g)
  4. washThe organic phase was washed with a mixture of water (100 g), sodium chloride (10 g), and sodium bicarbonate (7.5 g)
  5. dry with materialthe resultant organic layer was dried over anhydrous magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated

出典と根拠

ORDレコード
ord-1c5d6f3e9f13411cab9d4d7d0306d9c2
出典データセット
uspto-grants-1993_09
特許番号
US05243055

関連ノート

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