3-Pyridinecarboxaldehyde → 2-[3-[(Z)-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinylidene]methyl]pyridin-1-ium-1-yl]ethanol bromide

HRID 1724607Notes

Reaction equation

HRID 1724607 reaction equation
C1C=NC=[C:3]([CH:7]=[O:8])C=1.[CH3:9][N:10]1[C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][C:13]=2[S:12]/[C:11]/1=[N:19]/[N:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[N:24][CH:23]=1.[Br:28]C(O)C>C(#N)C>[Br-:28].[OH:8][CH2:7][CH2:3][N+:24]1[CH:25]=[CH:26][CH:27]=[C:22](/[CH:21]=[N:20]\[N:19]=[C:11]2\[S:12][C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][C:14]=3[N:10]\2[CH3:9])[CH:23]=1

Participants

5

Reactant 3

HCID 103713-PyridinecarboxaldehydeHCID 14202443Ethanol, 1-bromo-HCID 87882106(E)-3-methyl-N-(pyridin-3-ylmethylideneamino)-1,3-benzothiazol-2-imine

Product 1

HCID 876740722-[3-[(Z)-[(E)-(3-methyl-1,3-benzothiazol-2-ylidene)hydrazinylidene]methyl]pyridin-1-ium-1-yl]ethanol bromide

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1.21 g (4.51 mmol) of nicotine aldehyde ((2E)-3-methyl-1,3-benzothiazol-2(3H)-ylidene hydrazone from Step 1 and 0.85 g (6.76 mmol) of bromoethanol in acetonitrile were heated at reflux for 2 hours. After the solvent was removed, the precipitate was suction-filtered off, washed with ethyl acetate and dried under vacuum.

Workup

  1. temperatureat reflux for 2 hours
  2. customAfter the solvent was removed
  3. filtrationthe precipitate was suction-filtered off
  4. washwashed with ethyl acetate
  5. customdried under vacuum

Sources & evidence

ORD record
ord-3e6ee7708e93420a809ba01ad8980809
Source dataset
uspto-grants-2009_02
Patent number
US07488353B2

Reaction notes

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