Acetic Anhydride → N-[3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-yl]-acetamide

HRID 1906884Notes

Reaction equation

HRID 1906884 reaction equation
[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH2:19])[CH:17]=[CH:18][C:11]=2[O:10]1.[C:20](OC(=O)C)(=[O:22])[CH3:21]>N1C=CC=CC=1>[O:1]1[CH2:6][CH2:5][CH2:4][CH2:3][CH:2]1[O:7][CH2:8][CH:9]1[CH2:14][CH2:13][C:12]2[CH:15]=[C:16]([NH:19][C:20](=[O:22])[CH3:21])[CH:17]=[CH:18][C:11]=2[O:10]1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 202110563,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-amine

Product 1

HCID 20211054N-[3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-yl]-acetamideYield 82%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a stirred mixture of 5.3 parts of 3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-amine and 50 parts of pyridine were added dropwise 2.25 parts of acetic acid anhydride at a temperature below 10° C. Upon completion, stirring was continued for 10 minutes in an ice bath. The whole was stirred for 3 hours at room temperature. The reaction mixture was evaporated. Water was added to the residue. The product was extracted with 1,1'-oxybisethane. The organic layer was washed with water, dried, filtered and evaporated, yielding 5 parts (82%) of N-[3,4-dihydro-2-[[(tetrahydro-2H-pyran-2-yl)oxy]methyl]-2H-1-benzopyran-6-yl]-acetamide as an oily residue (intermediate 11).

Workup

  1. stirringThe whole was stirred for 3 hours at room temperature
  2. customThe reaction mixture was evaporated
  3. additionWater was added to the residue
  4. extractionThe product was extracted with 1,1'-oxybisethane
  5. washThe organic layer was washed with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated

Sources & evidence

ORD record
ord-3a57bd73f9bb4210b596c7a54e291b62
Source dataset
uspto-grants-1987_03
Patent number
US04654362

Reaction notes

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