2-Aminothiazole → HCID 62681258, compound

HRID 2243437Notes

Reaction equation

HRID 2243437 reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([OH:10])=O)=[CH:6][C:5]=1[F:13])([O-:3])=[O:2].O=S(Cl)Cl.[NH2:18][C:19]1[S:20][CH:21]=[CH:22][N:23]=1.CCN(C(C)C)C(C)C>C1(C)C=CC=CC=1.O1CCCC1.ClCCCl>[N+:1]([C:4]1[CH:12]=[CH:11][C:7]([C:8]([NH:18][C:19]2[S:20][CH:21]=[CH:22][N:23]=2)=[O:10])=[CH:6][C:5]=1[F:13])([O-:3])=[O:2]

Participants

8

Reactant 4

HCID 21552-AminothiazoleHCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 2306533-Fluoro-4-nitrobenzoic acid

Product 1

HCID 62681258HCID 62681258, compoundYield 35%

Reagents, catalysts & solvents 3

HCID 111,2-DichloroethaneSolventHCID 1140TolueneSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

4-Nitro-3-fluoro benzoic acid (535 mmol) was dissolved in toluene (500 mL) and tetrahydrofuran (THF) (75 mL). SOCl2 (930 mmol) was added and the mixture was heated at 65° C. for 5 h. The reaction mixture was cooled and the solvent removed by evaporation. The residue was re-dissolved in 1,2-dichloroethane. This solution was added dropwise to a suspension of 2-aminothiazole (480 mmol) and DIPEA (370 mmol) in 1,2-dichloroethane (1 L) with mechanical stirring, while the temperature was kept at 45° C. Upon complete addition the reaction mixture was heated at 60° C. for 1.5 h, then allowed to cool to room temperature and stirred over night. The reaction mixture was filtered, the solids were washed with 1,2-dichloroethane and dried in vacuo to give 4-nitro-3-fluoro-N-thiazol-2-yl-benzamide.

Workup

  1. temperatureThe reaction mixture was cooled
  2. customthe solvent removed by evaporation
  3. dissolutionThe residue was re-dissolved in 1,2-dichloroethane
  4. customwas kept at 45° C
  5. additionUpon complete addition the reaction mixture
  6. temperaturewas heated at 60° C. for 1.5 h
  7. temperatureto cool to room temperature
  8. filtrationThe reaction mixture was filtered
  9. washthe solids were washed with 1,2-dichloroethane
  10. customdried in vacuo

Sources & evidence

ORD record
ord-e382c69c9d694d4388865a9c7d78a73e
Source dataset
uspto-grants-2010_03
Patent number
US07674912B2

Reaction notes

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