Ammonium Acetate → HCID 178519127, compound

HRID 1909491Notes

Reaction equation

HRID 1909491 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C@H:8]2[CH2:13][CH2:12][C@H:11]([CH:14]=O)[CH2:10][CH2:9]2)=[CH:4][CH:3]=1.[C:16]1(=[O:27])[C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=2[C:19](=[O:26])[CH2:18][O:17]1.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C@H:8]2[CH2:9][CH2:10][C@H:11](/[CH:14]=[C:18]3\[O:17][C:16](=[O:27])[C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=4[C:19]\3=[O:26])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 517165Ammonium AcetateHCID 126956791H-2-Benzopyran-1,4(3H)-dioneHCID 178520920HCID 178520920, compound

Product 1

HCID 178519127HCID 178519127, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
70 °C

Procedure

To the resulting stirred mixture from stage 1, at ambient temperature under argon, was added acetic acid (125 mL), 1H-2-benzopyran-1,4(3H)-dione (compound of formula (III)) (16.2 g, 100 mmol) and ammonium acetate (7.7 g, 100 mmol). The reaction mixture was then heated to 70° C. and distilled for 2 hours. The resulting slurry was cooled to ambient temperature and water (75 mL) added. The slurry was stirred for 30 minutes at ambient temperature then filtered. The filter cake was washed with tert-butyl methyl ether (62.5 mL) and dried to give the title compound as a yellow solid (24.8 g). The material obtained was spectroscopically identical to that obtained in Stage 2, Example 3.

Workup

  1. distillationdistilled for 2 hours
  2. temperatureThe resulting slurry was cooled to ambient temperature
  3. additionwater (75 mL) added
  4. filtrationthen filtered
  5. washThe filter cake was washed with tert-butyl methyl ether (62.5 mL)
  6. customdried

Sources & evidence

ORD record
ord-16f3a601fa9547f4b2a7b60e2d326289
Source dataset
uspto-grants-2013_12
Patent number
US08598387B2

Reaction notes

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