4-(Dimethylamino)Benzaldehyde → HCID 67571141, compound

HRID 611443Notes

Reaction equation

HRID 611443 reaction equation
[Br-:1].[CH2:2]([N+:9]1[C:13]2[CH:14]=[CH:15][CH:16]=[CH:17][C:12]=2[S:11][C:10]=1[CH3:18])[C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][CH:4]=1.[CH3:19][N:20]([CH3:29])[C:21]1[CH:28]=[CH:27][C:24]([CH:25]=O)=[CH:23][CH:22]=1>C(OC(=O)C)(=O)C>[Br-:1].[CH3:19][N:20]([CH3:29])[C:21]1[CH:28]=[CH:27][C:24](/[CH:25]=[CH:18]/[C:10]2[S:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[N+:9]=2[CH2:2][C:3]2[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=2)=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 74794-(Dimethylamino)BenzaldehydeHCID 127928463-Benzyl-2-methyl-1,3-benzothiazol-3-ium bromide

Product 1

HCID 67571141HCID 67571141, compound

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-benzyl-2-methylbenzothiazol-3-ium bromide (0.30 g, 0.94 mmol) and 4-dimethylaminobenzaldehyde (0.21 g, 1.41 mmol) in 5 mL of acetic anhydride was heated under nitrogen. Upon refluxing, the mixture turned red and all solids appeared to be in solution. The solution was refluxed for 15 minutes, cooled, and filtered. The solid was washed with ethyl acetate to give (E)-2-[2-(4-dimethylaminophenyl)vinyl]-3-benzylbenzothiazol-3-ium bromide as a purple solid, mp 247-248° C., decomposed (dec).

Workup

  1. temperaturewas heated under nitrogen
  2. temperatureUpon refluxing
  3. temperatureThe solution was refluxed for 15 minutes
  4. temperaturecooled
  5. filtrationfiltered
  6. washThe solid was washed with ethyl acetate

Sources & evidence

ORD record
ord-13636e6d5f0246e8aa98cf9f11b002ba
Source dataset
uspto-grants-1999_12
Patent number
US06001331

Reaction notes

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