Acetic Anhydride → HCID 13851189, compound

HRID 978453Notes

Reaction equation

HRID 978453 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6](=[O:32])[N:7]([CH2:13][CH2:14][CH2:15][CH2:16][N:17]3[CH2:22][CH2:21][CH:20]([C:23](=[O:31])[C:24]4[CH:29]=[CH:28][C:27]([F:30])=[CH:26][CH:25]=4)[CH2:19][CH2:18]3)[C:8](=[O:12])[NH:9]2)=[CH:4][CH:3]=1.[C:33](OC(=O)C)(=[O:35])[CH3:34]>C(O)(=O)C>[F:30][C:27]1[CH:28]=[CH:29][C:24]([C:23]([CH:20]2[CH2:21][CH2:22][N:17]([CH2:16][CH2:15][CH2:14][CH2:13][N:7]3[C:6](=[O:32])[C:5]4[C:10](=[CH:11][C:2]([NH:1][C:33](=[O:35])[CH3:34])=[CH:3][CH:4]=4)[NH:9][C:8]3=[O:12])[CH2:18][CH2:19]2)=[O:31])=[CH:25][CH:26]=1

Participants

4

Reactant 2

HCID 7918Acetic AnhydrideHCID 13851173HCID 13851173, compound

Product 1

HCID 13851189HCID 13851189, compoundYield 100%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of 5.8 parts of 7-amino-3-[4-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl]-2,4(1H,3H)-quinazolinedione, 100 parts of acetic acid and 2.5 parts of acetic acid anhydride was stirred at reflux temperature. The reaction mixture was evaporated. The residue was stirred in water and ammonium hydroxide. The product was filtered off, washed with water and boiled in ethanol. After cooling, the product was filtered off, washed with 2,2'-oxybispropane and dried, yielding 6.3 parts (100%) of N-[3-[4-[4-(4-fluorobenzoyl)-1-piperidinyl]butyl]-1,2,3,4-tetrahydro-2,4-dioxo-7-quinazolinyl]-acetamide; mp. 273.1° C. (18).

Workup

  1. temperatureat reflux temperature
  2. customThe reaction mixture was evaporated
  3. stirringThe residue was stirred in water
  4. filtrationThe product was filtered off
  5. washwashed with water
  6. temperatureAfter cooling
  7. filtrationthe product was filtered off
  8. washwashed with 2,2'-oxybispropane
  9. customdried

Sources & evidence

ORD record
ord-08561e07173949c49060e62b4fda5fe9
Source dataset
uspto-grants-1987_05
Patent number
US04665075

Reaction notes

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