Carbon Dioxide → HCID 11033155, compound

HRID 1448674Notes

Reaction equation

HRID 1448674 reaction equation
[C:1]1([C:7]2OC(=O)[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:13]([C:19]([O:21][CH3:22])=[O:20])#[C:14][C:15]([O:17][CH3:18])=[O:16].C(=O)=O>ClC1C=CC=CC=1>[C:1]1([C:7]2[C:14]([C:15]([O:17][CH3:18])=[O:16])=[C:13]([C:19]([O:21][CH3:22])=[O:20])[S:9][N:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 280Carbon DioxideHCID 12980Dimethyl acetylenedicarboxylateHCID 8531705-phenyl-1,3,4-oxathiazol-2-one

Product 1

HCID 11033155HCID 11033155, compoundYield 61.6%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A solution of 412.2 g (2.3 mol) of 5-phenyl-1,3,4-oxathiazol-2-one, 662.7 g (4.66 mol) of dimethyl acetylenedicarboxylate, and 1 l. of chlorobenzene was heated at 135° for 6.5 hours, at which time CO2 evolution became very slow. Infrared and gas chromatography assays also indicated that the reaction was complete. The reaction mixture was concentrated under vacuum to 0.2 mm and 90°. The 680 g of pot residue was crystallized from about 700 ml of methanol to give 393 g of solid dimethyl 3-phenyl-4,5-isothiazoledicarboxylate, m.p. 70°-71.5°. An additional 69.9 g of solid, m.p. 70°-72°, was obtained from the filtrate. The total of 462.9 g amounted to a 72.7% yield.

Workup

  1. concentrationThe reaction mixture was concentrated under vacuum to 0.2 mm and 90°
  2. customThe 680 g of pot residue was crystallized from about 700 ml of methanol

Sources & evidence

ORD record
ord-3bced4bce74e43a9b4de41c932a2b344
Source dataset
uspto-grants-1980_02
Patent number
US04187099

Reaction notes

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