HuagongsheHuagongshe Chemistry Print Report · For research reference only
Methyl chloroacetate → Sodium Methoxide
Participants
| Role | Name | HCID | Charge |
|---|---|---|---|
| Reactant | Methyl chloroacetate | HCID 7295 | — |
| Reactant | Sodium Hydroxide | HCID 14798 | — |
| Reactant | 1,2-Benzisothiazol-3(2H)-one, 5-methoxy-, 1,1-dioxide | HCID 12381498 | — |
| Reactant | 2,6-Dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide | HCID 54694221 | — |
| Solvent | Toluene tert-butyl alcohol | HCID 22595558 | — |
| Product | Sodium Methoxide | HCID 10942334 | — |
| Product | Methyl 4-hydroxy-6-methoxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide | HCID 54713081 | — |
Reaction Steps
The starting compound was prepared by conversion of 5-methoxy-benzisothiazole-3(2H)-one-1,1-dioxide, analogous to 5-methyl-benzisothiazole-3(2H)-one-1,1-dioxide (see Example 8), with sodium hydroxide and methyl chloroacetate into methyl 5-methoxy-3-oxo-benzisothiazolo-2(3H)-acetate-1,1-dioxide. Methyl 4-hydroxy-6-methoxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide (m.p. 183° C., from ethyl acetate/cyclohexane) was obtained by subsequent rearrangement with sodium methylate in toluene/tert. butanol, and methyl 4-hydroxy-6-methoxy-2-methyl-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide was obtained by subsequent methylation.
Provenance & Evidence
| DOI | 10.6084/m9.figshare.5104873.v1 |
|---|---|
| Patent number | US04233299 |
| Source dataset | uspto-grants-1980_11 |
| ORD ID | ord-10286ad4ea454830bdb97ba4771b4efd |
| Source note | uspto-grants-1980_11 |