Dimethylformamide → Methyl 2-[(dimethylcarbamothioyl)-oxy]-4-methoxybenzoate

HRID 1249460ノート

反応式

HRID 1249460 の反応式
[OH:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N12CCN(CC1)CC2.CN(C)C=O.[CH3:27][N:28]([CH3:32])[C:29](Cl)=[S:30]>O>[CH3:27][N:28]([C:29](=[S:30])[O:1][C:2]1[CH:11]=[C:10]([O:12][CH3:13])[CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5])[CH3:32]

参加物

6

反応物 4

HCID 6228DimethylformamideHCID 9237DabcoHCID 27871Dimethylthiocarbamoyl chlorideHCID 79523Methyl 4-methoxysalicylate

生成物 1

HCID 13769567Methyl 2-[(dimethylcarbamothioyl)-oxy]-4-methoxybenzoate収率 76.5%

試薬・触媒・溶媒 1

HCID 962Water溶媒

反応条件

温度
50 °C

実験手順

To a mixture of 350 g of methyl 2-hydroxy-4-methoxybenzoate, 648 g of 1,4-diazabicyclo[2.2.2]-octane (DABCO) and 3 L of dimethylformamide was added 712 g of dimethylthiocarbamoyl chloride. The mixture was warmed to 50° C. and held for 7 hours, then allowed to cool overnight. The mixture was poured into 10 L water; the aqueous mixture was extracted with 8 L of benzene-hexane (4:1). The organic solution was washed with 1N HCl, 10% NaOH, and dried over magnesium sulfate. Evaporation of the solvent in vacuo gave 396 g of the title compound, m.p. 95°-105° C. Further extraction of the aqueous mixture gave additional product, 171 g, m.p. 117°-120° C. Recrystallization of a portion of the crude product from methanol gave pure material, m.p. 122°-124° C.

後処理

  1. temperatureto cool overnight
  2. extractionthe aqueous mixture was extracted with 8 L of benzene-hexane (4:1)
  3. washThe organic solution was washed with 1N HCl, 10% NaOH
  4. dry with materialdried over magnesium sulfate
  5. customEvaporation of the solvent in vacuo

出典と根拠

ORDレコード
ord-1baab6f9899a46e39fe5a42601d3522f
出典データセット
uspto-grants-1986_12
特許番号
US04632693

反応ノート

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