o-Vanillin → O-(2-Formyl-6-methoxyphenyl) dimethylcarbamothioate

HRID 2183660Notes

Reaction equation

HRID 2183660 reaction equation
[CH3:1][N:2]([CH3:6])[C:3](Cl)=[S:4].[CH3:7][O:8][C:9]1[C:10]([OH:17])=[C:11]([CH:14]=[CH:15][CH:16]=1)[CH:12]=[O:13].[OH-].[K+]>O1CCCC1.O>[CH3:1][N:2]([CH3:6])[C:3]([O:17][C:10]1[C:9]([O:8][CH3:7])=[CH:16][CH:15]=[CH:14][C:11]=1[CH:12]=[O:13])=[S:4]

Participants

6

Reactant 3

HCID 8991o-VanillinHCID 14797Potassium Hydroxide2×HCID 27871Dimethylthiocarbamoyl chloride

Product 1

HCID 13123229O-(2-Formyl-6-methoxyphenyl) dimethylcarbamothioateYield 54.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

A solution of N,N-dimethylthiocarbamoyl chloride (10 g) in tetrahydrofuran (40 ml) was added dropwise at <12° C. over 30 minutes to a stirred solution of 3-methoxy-2-hydroxybenzaldehyde (12.3 g) and potassium hydroxide (4.6 g) in water (105 ml) then the mixture was stirred at ambient temperature for 15 minutes. 10% Aqueous potassium hydroxide solution (30 ml) was added, then the product was extracted into toluene (3×150 ml). The combined extracts were washed with water (150 ml) then dried (MgSO4). The solvents were removed in vacuo and the residue was crystallised from methanol to give 2-(N,N-dimethylthiocarbamoyloxy)-3-methoxybenzaldehyde (10.5 g) as a yellow solid which was used without further purification.

Workup

  1. extractionthe product was extracted into toluene (3×150 ml)
  2. washThe combined extracts were washed with water (150 ml)
  3. dry with materialthen dried (MgSO4)
  4. customThe solvents were removed in vacuo
  5. customthe residue was crystallised from methanol

Sources & evidence

ORD record
ord-8a24918ac22f4197b29c8f79d03f4d06
Source dataset
uspto-grants-2005_05
Patent number
US06900216B2

Reaction notes

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