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

HRID 385035Notes

Reaction equation

HRID 385035 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.[C:20]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:35]#[N:36])[C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28])([CH3:23])([CH3:22])[CH3:21]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[C:20]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:35]#[N:36])[C:32]=1[O:33][CH3:34])[C:27]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:28])([CH3:23])([CH3:21])[CH3:22]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 96588BenzothiazolineHCID 866681523-t-Butyl-5-cyano-4-methoxybenzoyl chloride

Product 1

HCID 681089053-(3-t-Butyl-5-cyano-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 (943 mg) and 37% formalin (0.57 mL) in the same manner as in Example 1 was dissolved in chloroform (15 mL), and triethylamine (1.04 mL) and 3-t-butyl-5-cyano-4-methoxybenzoyl chloride (630 mg) was added to the solution, and then the mixture was stirred at room temperature for 1 hour. 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 (904 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-35069baedc784a70a70f2532f47b22db
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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