4-Dimethylamino-1-naphthaldehyde → (E)-2-[2-(4-dimethylaminonaphthalen-1-yl)vinyl]-3-heptylbenzothiazol-3-ium iodide

HRID 611445Notes

Reaction equation

HRID 611445 reaction equation
[I-: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])[CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8].[CH3:19][N:20]([CH3:33])[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24]([CH:31]=O)=[CH:23][CH:22]=1>C(OC(=O)C)(=O)C>[I-:1].[CH3:19][N:20]([CH3:33])[C:21]1[C:30]2[C:25](=[CH:26][CH:27]=[CH:28][CH:29]=2)[C:24](/[CH:31]=[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][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH3:8])=[CH:23][CH:22]=1

Participants

4

Reactant 2

HCID 6080524-Dimethylamino-1-naphthaldehydeHCID 675720163-Heptyl-2-methylbenzothiazolium iodide

Product 1

HCID 67571245(E)-2-[2-(4-dimethylaminonaphthalen-1-yl)vinyl]-3-heptylbenzothiazol-3-ium iodide

Reagents, catalysts & solvents 1

HCID 7918Acetic AnhydrideSolvent

Procedure

A mixture of 3-heptyl-2-methylbenzothiazolium iodide (0.50 g, 1.33 mmol) and 4-dimethylamino-1-naphthaldehyde (0.40 g, 2.01 mmol) in 5 mL of acetic anhydride under nitrogen was heated. Upon refluxing, the mixture turned purple and all solids seemed to be in solution. The solution was refluxed for 15 minutes and on cooling, solid formed. The mixture was filtered and washed with ethyl acetate to give (E)-2-[2-(4-dimethylaminonaphthalen-1-yl)vinyl]-3-heptylbenzothiazol-3-ium iodide as a dark brown solid, mp 195-197° C.

Workup

  1. temperaturewas heated
  2. temperatureUpon refluxing
  3. temperatureThe solution was refluxed for 15 minutes
  4. temperatureon cooling
  5. customsolid formed
  6. filtrationThe mixture was filtered
  7. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-e3e481c3262c42168acfaec6390db418
Source dataset
uspto-grants-1999_12
Patent number
US06001331

Reaction notes

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