Formaldehyde → 3-(3-Dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385111Notes

Reaction equation

HRID 385111 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.[CH3:20][N:21]([CH3:39])[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:35]([F:38])([F:37])[F:36])[C:32]=1[O:33][CH3:34])[C:27](Cl)=[O:28])=[O:23]>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH3:39][N:21]([CH3:20])[C:22]([C:24]1[CH:25]=[C:26]([CH:30]=[C:31]([C:35]([F:36])([F:38])[F:37])[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])=[O:23]

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 96588BenzothiazolineHCID 866681743-Dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl chloride

Product 1

HCID 681087933-(3-Dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8471TriethylamineSolvent

Procedure

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (214 mg) and 37% formalin (0.14 mL) in the same manner as in Example 1 was dissolved in chloroform (4 mL), and triethylamine (0.47 mL) and 3-dimethylcarbamoyl-4-methoxy-5-trifluoromethylbenzoyl chloride were 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 used for the synthesis of (g).

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 used for the synthesis of (g)

Sources & evidence

ORD record
ord-23f7dd08c3ae49518d72d25143e9b4e8
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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