5-Chlorosalicylic Acid → HCID 9843610, compound

HRID 644438Notes

Reaction equation

HRID 644438 reaction equation
[Cl:1][C:2]1[CH:10]=[C:6]([C:7]([OH:9])=O)[C:5]([OH:11])=[CH:4][CH:3]=1.[NH2:12][C:13]1[S:14][C:15]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:17]=1.P(Cl)(Cl)Cl>ClC1C=CC=CC=1>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:11])=[C:6]([CH:10]=1)[C:7]([NH:12][C:13]1[S:14][C:15]([C:22](=[O:27])[C:23]([CH3:26])([CH3:25])[CH3:24])=[C:16]([C:18]([CH3:20])([CH3:21])[CH3:19])[N:17]=1)=[O:9]

Participants

5

Reactant 3

HCID 94475-Chlorosalicylic AcidHCID 24387Phosphorus trichlorideHCID 85787172HCID 85787172, compound

Product 1

HCID 9843610HCID 9843610, compoundYield 48.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Procedure

A mixture of 5-chlorosalicylic acid (143.6 mg, 0.83 mmol), 2-amino-4-[(1,1-dimethyl)ethyl]-5-[(2,2-dimethyl)propionyl]thiazole (200.0 mg, 0.83 mmol), phosphorus trichloride (40 μl, 0.46 mmol) and chlorobenzene (4 mL) was refluxed for 3 hours. The residue obtained by concentration of the reaction mixture under reduced pressure was purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1) to give the title compound (159.1 mg, 48.4%) as a white powder.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customThe residue obtained by concentration of the reaction mixture under reduced pressure
  3. customwas purified by chromatography on silica gel (n-hexane:ethyl acetate=3:1)

Sources & evidence

ORD record
ord-102d7ed7327a42d78718c3c27290e46d
Source dataset
uspto-grants-2010_04
Patent number
US07700655B2

Reaction notes

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