HCID 21264460, compound → HCID 21264437, compound

HRID 567111Notes

Reaction equation

HRID 567111 reaction equation
[CH3:1][N:2]([CH3:18])[C:3]1[CH:8]=[CH:7][C:6]([CH:9]=[N:10][CH2:11][CH2:12][C:13]2[S:14][CH:15]=[CH:16][CH:17]=2)=[CH:5][CH:4]=1>C(O)(C(F)(F)F)=O>[CH3:18][N:2]([CH3:1])[C:3]1[CH:4]=[CH:5][C:6]([CH:9]2[C:17]3[CH:16]=[CH:15][S:14][C:13]=3[CH2:12][CH2:11][NH:10]2)=[CH:7][CH:8]=1

Participants

3

Reactant 1

HCID 21264460HCID 21264460, compound

Product 1

HCID 21264437HCID 21264437, compoundYield 95.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The above dimethyl-{4-[(2-thiophen-2-yl-ethylimino)-methyl]-phenyl}-amine (1 g, 3.9 mmol) was added TFA (20 mL) at once (strongly exothermic reaction). The reaction mixture was stirred at room temperature for 72 hours, then evaporated in vacuo. The crude oil was suspended in dichloromethane (75 ml) and extracted with 1 N hydrochloric acid (50 ml). The aqueous phase was added 2 N sodium hydroxide to pH=10, then extracted with dichloromethane (3×125 ml). The organic phase was dried with MgSO4, filtered, evaporated in vacuo to afford 0.96 g (95%) of the title compound.

Workup

  1. customstrongly exothermic reaction)
  2. customevaporated in vacuo
  3. extractionextracted with 1 N hydrochloric acid (50 ml)
  4. additionThe aqueous phase was added 2 N sodium hydroxide to pH=10
  5. extractionextracted with dichloromethane (3×125 ml)
  6. dry with materialThe organic phase was dried with MgSO4
  7. filtrationfiltered
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-328ea1727bd24068930e07d5a1a47723
Source dataset
uspto-grants-2001_01
Patent number
US06177443B1

Reaction notes

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