Formaldehyde → HCID 68108741, compound

HRID 385092Notes

Reaction equation

HRID 385092 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(N(C(C)C)CC)(C)C.[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([I:41])[C:38]=1[O:39][CH3:40])[C:33](Cl)=[O:34]>ClCCl>[Cl:29][C:30]1[CH:31]=[C:32]([CH:36]=[C:37]([I:41])[C:38]=1[O:39][CH3:40])[C:33]([N:3]1[C:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=2[S:1][CH2:2]1)=[O:34]

Participants

7

Reactant 5

HCID 712FormaldehydeHCID 87132-AminothiophenolHCID 81531DiisopropylethylamineHCID 96588BenzothiazolineHCID 33779668HCID 33779668, compound

Product 1

HCID 68108741HCID 68108741, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2,3-dihydro-1,3-benzothiazole synthesized from 2-aminobenzenethiol (1.65 g) and 37% formalin (1.09 mL) in the same manner as in Example 1 was dissolved in dichloromethane (15 mL), and diisopropylethylamine (3.0 mL) and 3-chloro-5-iodo-4-methoxybenzoyl chloride (3.05 g) 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 crystallized from a mixture of n-hexane and ethyl acetate in a mixing ratio of 1:1 to obtain the title compound (2.44 g) as a pale yellow solid.

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 crystallized from a mixture of n-hexane and ethyl acetate in a mixing ratio of 1:1

Sources & evidence

ORD record
ord-223a3e50df75447aa275846600431ece
Source dataset
uspto-grants-2013_02
Patent number
US08367843B2

Reaction notes

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