Trimethyl orthoformate → 2,2-Dimethyl-5-((4-methylthiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dione

HRID 911922Notes

Reaction equation

HRID 911922 reaction equation
[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[CH2:5][C:4](=[O:9])[O:3]1.[CH3:11]OC(OC)OC.[CH3:18][C:19]1[C:20]([NH2:24])=[CH:21][S:22][CH:23]=1>>[CH3:1][C:2]1([CH3:10])[O:7][C:6](=[O:8])[C:5](=[CH:11][NH:24][C:20]2[C:19]([CH3:18])=[CH:23][S:22][CH:21]=2)[C:4](=[O:9])[O:3]1

Participants

4

Reactant 3

HCID 9005Trimethyl orthoformate2×HCID 162492,2-Dimethyl-1,3-dioxane-4,6-dioneHCID 57433964-Methylthiophen-3-amine

Product 1

HCID 669953662,2-Dimethyl-5-((4-methylthiophen-3-ylamino)methylene)-1,3-dioxane-4,6-dioneYield 99%

Conditions

Temperature
90 °C

Procedure

A stirred solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (4.85 g, 34 mmol) in trimethoxymethane (37 mL, 337 mmol) was heated to 90° C. under nitrogen. After 2 hours, a solution was 4-methylthiophen-3-amine (3.81 g, 34 mmol) was added (as a solution in trimethoxymethane (37 mL, 337 mmol). The reaction stirred at 90° C. for 6 hours and then was allowed to cool to room temperature and concentrated. The material was placed in the refrigerator where it solidified after two days to obtain the title compound (9 g, quantitative).

Workup

  1. temperatureto cool to room temperature
  2. concentrationconcentrated
  3. waitsolidified after two days

Sources & evidence

ORD record
ord-798b7dc8904d4ced8a8b7b489eb2b41a
Source dataset
uspto-grants-2011_09
Patent number
US08022223B2

Reaction notes

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