Furfural → 2-Furfurylideneamino-4-methyl-5-methylsulfonylbenzoic acid

HRID 1606604ノート

反応式

HRID 1606604 の反応式
[CH:1](=O)[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][C:9]1[CH:10]=[C:11]([NH2:22])[C:12](=[CH:16][C:17]=1[S:18]([CH3:21])(=[O:20])=[O:19])[C:13]([OH:15])=[O:14]>>[CH:1](=[N:22][C:11]1[CH:10]=[C:9]([CH3:8])[C:17]([S:18]([CH3:21])(=[O:20])=[O:19])=[CH:16][C:12]=1[C:13]([OH:15])=[O:14])[C:2]1[O:6][CH:5]=[CH:4][CH:3]=1

参加物

3

反応物 2

HCID 7362FurfuralHCID 215439954-Methyl-5-methylsulfonylanthranilic acid

生成物 1

HCID 215439602-Furfurylideneamino-4-methyl-5-methylsulfonylbenzoic acid

反応条件

温度
80 °C

実験手順

This product is prepared by replacing the 2,4-dichloro-5-chlorosulfonylbenzoic acid employed in Example 1, Step A, by an equimolecular proportion of 4-methyl-5-chlorosulfonylanthranilic acid and then following substantially the same procedure described in Example 1, Steps A and B, there is obtained 4-methyl-5-methylsulfonylanthranilic acid employed in the following step without purification. The compound thus obtained is combined with excess furfural and heated on a water bath at about 80° C. The water formed during the reaction is removed by azeotropic distillation with the excess furfural at about 15 mm. Hg. pressure over a one hour period. The 2-furfurylideneamino-4-methyl-5-methylsulfonylbenzoic acid formed is stirred while cooling in acetic acid while a mixture of trimethylamine-borane complex in acetic acid is added over a 10 minute period. The reaction mixture then is heated on the steam bath for 5-10 minutes, then quenched in ice water to give 2-furfurylamino-4-methyl-5-methylsulfonylbenzoic acid.

後処理

  1. customemployed in the following step without purification
  2. customThe compound thus obtained
  3. customis removed by azeotropic distillation with the excess furfural at about 15 mm. Hg

出典と根拠

ORDレコード
ord-6bf35b954a3b4790a4ae35e0783feafd
出典データセット
uspto-grants-1976_04
特許番号
US03953476

反応ノート

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