Ethyl chloroacetate → 3-Oxo-naphth[2,1-d]isothiazoline-2-acetic acid ethyl ester-1,1-dioxide

HRID 1730567Notes

Reaction equation

HRID 1730567 reaction equation
[Na].[O:2]=[C:3]1[C:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]=2[S:5](=[O:17])(=[O:16])[NH:4]1)=[CH:14][CH:13]=[CH:12][CH:11]=3.[CH2:18]([O:20][C:21](=[O:24])[CH2:22]Cl)[CH3:19]>C(O)C>[CH2:18]([O:20][C:21](=[O:24])[CH2:22][N:4]1[C:3](=[O:2])[C:7]2[CH:8]=[CH:9][C:10]3[C:15]([C:6]=2[S:5]1(=[O:17])=[O:16])=[CH:14][CH:13]=[CH:12][CH:11]=3)[CH3:19]

Participants

5

Reactant 3

HCID 7751Ethyl chloroacetateHCID 5360545SodiumHCID 124215141H-1lambda~6~-Naphtho[2,1-d][1,2]thiazole-1,1,3(2H)-trione

Product 1

HCID 124215153-Oxo-naphth[2,1-d]isothiazoline-2-acetic acid ethyl ester-1,1-dioxideYield 72%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

3-Oxo-naphth[2,1-d]isothiazoline-2-acetic acid ethyl ester -1,1-dioxide was prepared analogous to Example 1a from the sodium salt of 3-oxo-naphth[2,1-d]isothiazoline-1,1-dioxide and chloro-acetic acid ethyl ester. Yield: 72% of theory; m.p. 149- 150.5° C (from ethanol).

Sources & evidence

ORD record
ord-3e7481bec7cb474f87ede5065056a779
Source dataset
uspto-grants-1976_11
Patent number
US03992535

Reaction notes

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