Methyl chloroacetate → Sodium Methoxide

HRID 224602Notes

Reaction equation

HRID 224602 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:10](=[O:12])(=[O:11])[NH:9][C:8](=[O:13])[C:7]=2[CH:14]=1.CN1C([C:22](NC2SC(C)=CN=2)=[O:23])=C(O)C2C=C(C)C=CC=2S1(=O)=O.[OH-].[Na+:40].Cl[CH2:42][C:43]([O:45][CH3:46])=[O:44]>C1(C)C=CC=CC=1.C(O)(C)(C)C>[OH:13][C:8]1[C:7]2[CH:14]=[C:3]([O:2][CH3:1])[CH:4]=[CH:5][C:6]=2[S:10](=[O:12])(=[O:11])[NH:9][C:42]=1[C:43]([O:45][CH3:46])=[O:44].[CH3:22][O-:23].[Na+:40]

Participants

7

Reactant 4

HCID 7295Methyl chloroacetateHCID 14798Sodium HydroxideHCID 123814981,2-Benzisothiazol-3(2H)-one, 5-methoxy-, 1,1-dioxideHCID 546942212,6-Dimethyl-4-hydroxy-N-(5-methyl-2-thiazolyl)-2H-1,2-benzothiazine-3-carboxamide-1,1-dioxide

Product 2

HCID 10942334Sodium MethoxideHCID 54713081Methyl 4-hydroxy-6-methoxy-2H-1,2-benzothiazine-3-carboxylate-1,1-dioxide

Reagents, catalysts & solvents 1

HCID 22595558Toluene tert-butyl alcoholSolvent

Procedure

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.

Sources & evidence

ORD record
ord-10286ad4ea454830bdb97ba4771b4efd
Source dataset
uspto-grants-1980_11
Patent number
US04233299

Reaction notes

Loading…