関与物質
| 役割 | 名称 | HCID | 仕込み量 |
|---|
| 反応物 | Sulfur Dioxide | HCID 1119 | — |
| 反応物 | Ammonium Hydroxide | HCID 14923 | — |
| 反応物 | Sulfuryl chloride | HCID 24648 | — |
| 反応物 | Methyl 2-amino-6-chlorobenzoate | HCID 592849 | — |
| 反応物 | 4-Methyl-1H-1lambda~6~,2-benzothiazole-1,1,3(2H)-trione | HCID 15934075 | — |
| 反応物 | Sodium Nitrite | HCID 23668193 | — |
| 溶媒 | Acetic Acid | HCID 176 | — |
| 溶媒 | Hydrochloric Acid | HCID 313 | — |
| 溶媒 | Water | HCID 962 | — |
| 生成物 | 4-Chloro-2,3-dihydro-1lambda6,2-benzothiazole-1,1,3-trione | HCID 15567171 | 62% |
反応手順
4-Chlorosaccharin was prepared by the same method as used for preparing 4-methylsaccharin using methyl 6-chloro-anthranilate (4.22 g; 22.7 mmol) in acetic acid (22 ml) and conc. HCl (40 ml) and sodium nitrite (1.68 g; 24.3 mmol) in water (7 ml) to prepare the diazonium salt which was added to cupric chloride dihydrate (1.93 g; 11.4 mmol; 0.5 equiv.) and sulfur dioxide (6.5 g; excess) in acetic acid (30 ml)/water (5 ml). The resulting sulfonyl chloride was treated with ammonium hydroxide (150 ml) as previously described to afford 3.07 g (62%) of 4-chlorosaccharin as a pale yellow solid, mp 245°-246° C. 1H nmr (300 MHz, CD3CN): 7.918 (1H, dd, J=7.39, 1.91 Hz); 7.865 (1H, t, J-7.52 Hz); 7.829 (1H, br d, J=7.30 Hz). IR (KBr, CM1): 3570 (s); 3520 (s); 2950 (s,b); 1735 (s); 1630 (m). FDMS: m/e 217 (M+).
情報源と証拠
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|
| 特許番号 | US05650422 |
|---|
| 出典データセット | uspto-grants-1997_07 |
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| ORD ID | ord-d9379b30933d4427956c059762150bdc |
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| 出典メモ | uspto-grants-1997_07 |
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