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

HRID 385026Notes

Reaction equation

HRID 385026 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]([C:32]#[N:33])[C:29]=1[O:30][CH3:31])[C:24](Cl)=[O:25]>ClCCl.C(N(CC)CC)C>[Cl:20][C:21]1[CH:22]=[C:23]([CH:27]=[C:28]([C:32]#[N:33])[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 866681513-Chloro-5-cyano-4-methoxybenzoyl chloride

Product 1

HCID 681080913-(3-Chloro-5-cyano-4-methoxybenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8471TriethylamineSolvent

Procedure

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (810 mg) and 37% formalin (0.53 mL) in the same manner as in the synthesis of Example 1 was dissolved in dichloromethane (15 mL), and triethylamine (1.90 mL) and 3-chloro-5-cyano-4-methoxybenzoyl chloride (993 mg) were added to the solution, and then the mixture was stirred at room temperature for 1.5 hours. 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=6:1) to obtain the title compound (580 mg) as a 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=6:1)

Sources & evidence

ORD record
ord-3a4c5c0016894adea52ef0fdf4e0fd76
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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