1,3-Thiazole-2-carbaldehyde → [3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-thiazol-2-ylmethyleneamine

HRID 1620964Notes

Reaction equation

HRID 1620964 reaction equation
[CH3:1][CH:2]([CH3:15])[CH2:3][CH:4]([NH2:14])[C:5]12[O:12][CH2:11][C:8]([CH3:13])([CH2:9][O:10]1)[CH2:7][O:6]2.[S:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=O>C1C=CC=CC=1>[CH3:1][CH:2]([CH3:15])[CH2:3][CH:4]([N:14]=[CH:21][C:17]1[S:16][CH:20]=[CH:19][N:18]=1)[C:5]12[O:6][CH2:7][C:8]([CH3:13])([CH2:9][O:10]1)[CH2:11][O:12]2

Participants

4

Reactant 2

HCID 27349031,3-Thiazole-2-carbaldehydeHCID 574469573-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butylamine

Product 1

HCID 67298572[3-Methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-thiazol-2-ylmethyleneamine

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

A solution of 3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butylamine (1.9 g, 8.8 mmol) and thiazole-2-carboxaldehyde (998 mg, 8.8 mmol) in benzene was refluxed for 3 h using a Dean-Stark trap, during which time water was collected and the remaining residue was evaporated under reduced pressure to get [3-methyl-1-(4-methyl-2,6,7-trioxa-bicyclo[2.2.2]oct-1-yl)-butyl]-thiazol-2-ylmethyleneamine as an orange solid.

Workup

  1. customduring which time water was collected
  2. customthe remaining residue was evaporated under reduced pressure

Sources & evidence

ORD record
ord-d909da9538174533959f1b729301240e
Source dataset
uspto-grants-2014_07
Patent number
US08772336B2

Reaction notes

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