Ammonium Acetate → HCID 13749916, compound

HRID 2290662Notes

Reaction equation

HRID 2290662 reaction equation
[C:1]([C:5]1[C:10]([O:11][CH3:12])=[C:9]([O:13][CH3:14])[CH:8]=[C:7]([Cl:15])[C:6]=1[NH:16][C:17]([O:19]C)=O)(OC)=[O:2].C([O-])(=O)C.[NH4+:25]>>[Cl:15][C:7]1[CH:8]=[C:9]([O:13][CH3:14])[C:10]([O:11][CH3:12])=[C:5]2[C:6]=1[NH:16][C:17](=[O:19])[NH:25][C:1]2=[O:2]

Participants

3

Reactant 2

HCID 517165Ammonium AcetateHCID 20231660HCID 20231660, compound

Product 1

HCID 13749916HCID 13749916, compoundYield 49%

Conditions

Temperature
128 °C

Procedure

A mixture of 1.21 g (4.0 mmol) of methyl 2-carbomethoxy-6-chloro-3,4-dimethoxybenzenecarbamate and 3.17 g (20 mmol) of ammonium acetate was prepared and heated to 128° C. A solution was obtained and after one hour a white solid precipitated. The reaction mixture was cooled to room temperature, 25 mL of water was added, and the reaction mixture was cooled to 5° C. The product was filtered and washed with 2×5 mL of distilled water and 1×10 mL of methanol. Drying under vacuum gave 500 mg (49%) of white product, mp 286°-289° C. NMR (TFA) δ 4.02 (s, 3H, OCH3), 4.12 (s, 3H, OCH3), 7.60 (s, 1H, ArH), 9.68 (br s, 1H, NH).

Workup

  1. customwas prepared
  2. customA solution was obtained and after one hour a white solid
  3. customprecipitated
  4. temperatureThe reaction mixture was cooled to room temperature
  5. addition25 mL of water was added
  6. temperaturethe reaction mixture was cooled to 5° C
  7. filtrationThe product was filtered
  8. washwashed with 2×5 mL of distilled water and 1×10 mL of methanol
  9. customDrying under vacuum

Sources & evidence

ORD record
ord-5a58c9568a8044da841dc355b42a7b56
Source dataset
uspto-grants-1986_10
Patent number
US04617417

Reaction notes

Loading…