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Formaldehyde → 3-(4-Benzyloxy-3-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

HRID 385116
Notes
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Reaction equation

HRID 385116 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.[CH2:20]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32](Cl)=[O:33])=[CH:30][C:29]=1[C:37]([F:40])([F:39])[F:38])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>C(Cl)(Cl)Cl.C(N(CC)CC)C>[CH2:20]([O:27][C:28]1[CH:36]=[CH:35][C:31]([C:32]([N:3]2[C:4]3[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=3[S:1][CH2:2]2)=[O:33])=[CH:30][C:29]=1[C:37]([F:38])([F:39])[F:40])[C:21]1[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 96588BenzothiazolineHCID 866681754-Benzyloxy-3-trifluoromethylbenzoyl chloride

Product 1

HCID 681089763-(4-Benzyloxy-3-trifluoromethylbenzoyl)-2,3-dihydro-1,3-benzothiazole

Reagents, catalysts & solvents 2

HCID 6212
Chloroform
Solvent
HCID 8471TriethylamineSolvent

Procedure

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (282 mg) and 37% formalin (0.19 mL) in the same manner as in Example 1 was dissolved in chloroform (6 mL), and triethylamine (0.62 mL) and 4-benzyloxy-3-trifluoromethylbenzoyl chloride were added to the solution, and then the mixture was stirred at mom 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=4:1) 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=4:1)

Sources & evidence

ORD record
ord-20241d3e0d9f4098ac481fe66ad2b1ea
Source dataset
uspto-grants-2013_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08367843B2

Reaction notes

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