Acetic Acid → HCID 178519127, compound

HRID 1909493Notes

Reaction equation

HRID 1909493 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(O)(=O)C.[C:20]1(=[O:31])[C:25]2[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=2[C:23](=[O:30])[CH2:22][O:21]1.N1CCOCC1>O>[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:22]3\[O:21][C:20](=[O:31])[C:25]4[CH:26]=[CH:27][CH:28]=[CH:29][C:24]=4[C:23]\3=[O:30])[CH2:12][CH2:13]2)=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 8083MorpholineHCID 126956791H-2-Benzopyran-1,4(3H)-dioneHCID 178520920HCID 178520920, compound

Product 1

HCID 178519127HCID 178519127, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
40 °C

Procedure

To the resulting stirred mixture from stage 1, at ambient temperature under argon, was added acetic acid (250 mL), 1H-2-benzopyran-1,4(3H)-dione (compound of formula (III)) (32.4 g, 200 mmol) and morpholine (17.5 mL, 200 mmol). The reaction mixture was heated to 40° C. for 4 hours then allowed to cool to ambient temperature and stir overnight. Water (250 mL) was added and the slurry stirred for 15 minutes at ambient temperature then filtered. The filter cake was washed twice with tert-butyl methyl ether (2×125 mL) and dried to give the title compound as a yellow solid (62.4 g). The material obtained was spectroscopically identical to that obtained in Stage 2, Example 3.

Workup

  1. temperatureto cool to ambient temperature
  2. stirringthe slurry stirred for 15 minutes at ambient temperature
  3. filtrationthen filtered
  4. washThe filter cake was washed twice with tert-butyl methyl ether (2×125 mL)
  5. customdried

Sources & evidence

ORD record
ord-468385e9c4ce47c5adcdaf789558130a
Source dataset
uspto-grants-2013_12
Patent number
US08598387B2

Reaction notes

Loading…