Acetone → HCID 22902368, compound

HRID 1078363Notes

Reaction equation

COC1C=C([C:9]2[CH:17]=[CH:16][CH:15]=[CH:14][C:10]=2[C:11]([NH2:13])=[S:12])C=CC=1.[C:18](Cl)(=[O:22])[C:19](Cl)=[O:20].C[C:25](C)=[O:26]>>[CH3:25][O:26][C:15]1[CH:14]=[C:10]([C:11]2[S:12][C:18](=[O:22])[C:19](=[O:20])[N:13]=2)[CH:9]=[CH:17][CH:16]=1

Participants

Reactant 3

HCID 180Acetone2×

HCID 65578Oxalyl chloride

HCID 22902353HCID 22902353, compound

Product 1

HCID 22902368HCID 22902368, compound

Conditions

Temperature: -20 °C

Procedure

7.3 g of 3-methoxyphenylthiobenzamide [preparation similar to Example 65 B)] were dissolved in 50 ml acetone and cooled to -20° C. in a nitrogen atmosphere. A solution of 4 ml oxalyl chloride in 40 ml acetone were added slowly dropwise to this solution. Then it was stirred for 1 hour at 20° C. The crystals that settled out were drawn off and the mother liquor concentrated to approximately one-third of the original volume. A further crystal fraction was obtained. In all, 5 g of 2-(3-methoxyphenyl)-1,3-thiazole -4,5-dione were obtained as a yellow solid.

Workup

concentrationthe mother liquor concentrated to approximately one-third of the original volume
customA further crystal fraction was obtained

Sources & evidence

ORD record: ord-02d6fb8a59e24d5c90c63b2117f2a26a
Source dataset: uspto-grants-1996_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05547967

Reaction notes

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