Water → HCID 178426082, compound

HRID 2090044Notes

Reaction equation

HRID 2090044 reaction equation
CC1(C)O[C:6](=O)[CH2:5][C:4](=O)[O:3]1.C(OC)(OC)OC.[Cl:18][C:19]1[CH:25]=[C:24]([CH3:26])[C:22]([NH2:23])=[CH:21][CH:20]=1.O>CN(C=O)C>[Cl:18][C:19]1[CH:20]=[C:21]2[C:22](=[C:24]([CH3:26])[CH:25]=1)[N:23]=[CH:6][CH:5]=[C:4]2[OH:3]

Participants

6

Reactant 4

HCID 962WaterHCID 72514-Chloro-2-toluidineHCID 9005Trimethyl orthoformateHCID 162492,2-Dimethyl-1,3-dioxane-4,6-dione

Product 1

HCID 178426082HCID 178426082, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of 2,2-dimethyl-1,3-dioxane-4,6-dione (1.58 g, 11.0 mmol) in trimethyl orthoformate (10 mL, 90 mmol) was refluxed for one hour. The mixture was cooled slightly, then a solution of 4-chloro-6-methylaniline (1.4 g, 10 mmol) in DMF (10 mL) was added. The mixture was refluxed for 2 hours then cooled to room temperature. The mixture was poured into cold water (150 mL) then extracted with EtOAc. The organic phase was washed with water then saturated NaCl (aq), dried over Na2SO4, filtered, then concentrated. The resulting light yellow, crystalline solid was used directly for the following step. LC4: 2.14 min. (M+H) 296.

Workup

  1. temperatureThe mixture was cooled slightly
  2. temperatureThe mixture was refluxed for 2 hours
  3. extractionthen extracted with EtOAc
  4. washThe organic phase was washed with water
  5. dry with materialsaturated NaCl (aq), dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custom2.14 min. (M+H) 296

Sources & evidence

ORD record
ord-b5036bd4527949ff97fbf808fe87ed70
Source dataset
uspto-grants-2013_05
Patent number
US08436015B2

Reaction notes

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