Formaldehyde → 3-(3-Chloro-5-fluoro-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385083Notes

Reaction equation

HRID 385083 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH2:2]1.NC1C=CC=CC=1S.C=O.[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([F:32])[C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([F:32])[C:29]=1[O:30][CH3:31])[C:24]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:25]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 96588BenzothiazolineHCID 37390793-Chloro-5-fluoro-4-methoxybenzoyl chloride

Product 1

HCID 681083653-(3-Chloro-5-fluoro-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (346 mg) and 37% formalin (0.23 mL) in the same manner as in Example 1 was dissolved in chloroform (3 mL), and triethylamine (0.38 mL) and 3-chloro-5-fluoro-4-methoxybenzoyl chloride were added to the solution, and then the mixture was stirred at room temperature for 90 minutes. The solvent was distilled off under reduced pressure and water was added, and then the mixture was extracted with ethyl acetate. The organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine, and then dried over anhydrous sodium sulfate. The solvent was distilled off under reduced pressure and the obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1) to obtain the title compound (356 mg) as a pale yellow oily substance.

Workup

  1. distillationThe solvent was distilled off under reduced pressure and water
  2. additionwas added
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe organic layer was washed with 1N hydrochloric acid, 1N sodium hydroxide and saturated brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off under reduced pressure
  7. customthe obtained residue was purified by silica gel column chromatography (n-hexane:ethyl acetate=8:1)

Sources & evidence

ORD record
ord-e2a1e87d7dd443c682e8219c794a888e
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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