Ammonium Hydroxide → Ethoxzolamide

HRID 345775ノート

反応式

HRID 345775 の反応式
[OH-:1].[NH4+:2].[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([SH:13])[S:12][C:8]=2[CH:7]=1)[CH3:4].[O-:16]Cl.[Na+]>[OH-].[Na+]>[CH2:3]([O:5][C:6]1[CH:15]=[CH:14][C:9]2[N:10]=[C:11]([S:13]([NH2:2])(=[O:16])=[O:1])[S:12][C:8]=2[CH:7]=1)[CH3:4]

参加物

5

反応物 3

HCID 14923Ammonium Hydroxide2 回HCID 23665760Sodium HypochloriteHCID 178466040HCID 178466040、化合物

生成物 1

HCID 3295Ethoxzolamide収率 59.7%

試薬・触媒・溶媒 1

HCID 14798Sodium Hydroxide溶媒

反応条件

温度
0 °C

実験手順

A solution of ammonium hydroxide (650 mL) was cooled to 0° C. in an ice/methanol bath. A solution containing 6-ethoxy-2-mercapto-benzothiazole (16.0 g, 0.076 mol) in 170 mL of 5% NaOH and a solution of 5.25% NaOCl (150 mL) were added simultaneously to the ammonium hydroxide solution while maintaining a temperature of 0° C. The reaction was stirred for 15 min. upon completing the addition, and the sulfenamide was collected by vacuum filtration. The sulfenamide was dissolved in 1 L of acetone and oxidized by the addition of 450 mL of 5% KMn04 over 4 hours. The MnO2 was removed by filtering through Celite, and the acetone was removed under vacuum. The product was precipitated from solution by acidification with concentrated HCl to yield 11.7 g (59.7%) of 6-ethoxy-2-benzothiazolesulfonamide, which was purified by dissolving it in 5% NaOH, filtering, and precipitating with concentrated HCl; mp 190°-191° C.; MS, m/e 258 (M,calcd 258).

後処理

  1. additionthe addition
  2. filtrationthe sulfenamide was collected by vacuum filtration
  3. dissolutionThe sulfenamide was dissolved in 1 L of acetone
  4. additionoxidized by the addition of 450 mL of 5% KMn04 over 4 hours
  5. customThe MnO2 was removed
  6. filtrationby filtering through Celite
  7. customthe acetone was removed under vacuum
  8. customThe product was precipitated from solution by acidification with concentrated HCl

出典と根拠

ORDレコード
ord-724d7f35a98b4fadb472c61d618182eb
出典データセット
uspto-grants-1991_10
特許番号
US05059613

反応ノート

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