Dimethyl acetylenedicarboxylate → Dimethyl 3-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-Isothiazoledicarboxylate

HRID 443704Notes

Reaction equation

HRID 443704 reaction equation
[F:1][C:2]([F:20])([F:19])[C:3]1[CH:4]=[C:5]([C:13]2OC(=O)[S:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[C:21]([C:27]([O:29][CH3:30])=[O:28])#[C:22][C:23]([O:25][CH3:26])=[O:24]>ClC1C=CC=CC=1Cl>[F:19][C:2]([F:20])([F:1])[C:3]1[CH:4]=[C:5]([C:13]2[C:22]([C:23]([O:25][CH3:26])=[O:24])=[C:21]([C:27]([O:29][CH3:30])=[O:28])[S:15][N:14]=2)[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=1

Participants

4

Reactant 2

HCID 12980Dimethyl acetylenedicarboxylateHCID 124374035-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-one

Product 1

HCID 12437420Dimethyl 3-(alpha,alpha,alpha,alpha',alpha',alpha'-Hexafluoro-3,5-Xylyl)-4,5-IsothiazoledicarboxylateYield 77%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 20.7 g (0.0657 mol) of 5-(α,α,α,α',α',α'-hexafluoro-3,5-xylyl)-1,3,4-oxathiazol-2-one and 18.7 g (0.131 mol) of dimethyl acetylenedicarboxylate in 52 g of o-dichlorobenzene was held at reflux for 10 hours (gas chromatography assay revealed the product had formed in 77% yield) and was concentrated under vacuum to 90° at 0.5 torr. The residue was crystallized from methanol to give 17.9 g of solid, m.p. 71°-74°. The solid was recrystallized to give 14.3 g (53% yield) of white solid, m.p. 73°-75°.

Workup

  1. temperatureat reflux for 10 hours (gas chromatography assay
  2. customhad formed in 77% yield) and
  3. concentrationwas concentrated under vacuum to 90° at 0.5 torr
  4. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-c95cf3037ab9405fbb84db090ccf7342
Source dataset
uspto-grants-1981_04
Patent number
US04261728

Reaction notes

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