p-Toluenesulfonic acid → HCID 18324465, compound

HRID 1251928Notes

Reaction equation

HRID 1251928 reaction equation
[S:1]1[CH:5]=[CH:4][N:3]=[C:2]1C=O.C(O[CH:11]([O:15][CH2:16][CH3:17])[O:12][CH2:13][CH3:14])C.C1(C)C=CC(S(O)(=O)=O)=CC=1.C(=O)(O)[O-].[Na+]>C(O)C>[CH2:16]([O:15][CH:11]([C:2]1[S:1][CH:5]=[CH:4][N:3]=1)[O:12][CH2:13][CH3:14])[CH3:17]

Participants

6

Reactant 4

HCID 6101p-Toluenesulfonic acid2×HCID 31214Ethyl orthoformateHCID 516892Sodium BicarbonateHCID 27349031,3-Thiazole-2-carbaldehyde

Product 1

HCID 18324465HCID 18324465, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 2-thiazole carboxaldehyde (25 g, 221 mmol), triethylorthoformate (46 mls, 41 g, 276 mmol) and para-toluenesulphonic acid (1.52 g, 9 mmol) in ethanol (200 ml) was sured for 16 hours under a nitrogen atmosphere at ambient temperature. A further amount of para-toluenesulphonic acid (2 g, 11 mmol) was added and the reaction stirred for another 16 hours. The mixture was treated with sodium bicarbonate to pH 9, stirred for a further 5 minutes and then filtered and the filtrate evaporated to dryness to give 2-(1,1-diethoxymethyl)thiazole as a clear oil, which was used without flirher purification (41 g, 99%).

Workup

  1. stirringstirred for a further 5 minutes
  2. filtrationfiltered
  3. customthe filtrate evaporated to dryness

Sources & evidence

ORD record
ord-77b1478b1c8447dab5a79f5b049d61ea
Source dataset
uspto-grants-2002_01
Patent number
US06342765B1

Reaction notes

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