Acetic Anhydride → HCID 21428838, compound

HRID 437666Notes

Reaction equation

HRID 437666 reaction equation
[NH2:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:26][CH2:25][C:12]2([N:16]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[CH2:15][NH:14][C:13]2=[O:24])[CH2:11][CH2:10]1)=[O:5].[C:32](OC(=O)C)(=[O:34])[CH3:33].[OH-].[NH4+]>O>[C:32]([NH:1][C:2]1[CH:30]=[C:29]([F:31])[CH:28]=[CH:27][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:9]1[CH2:26][CH2:25][C:12]2([N:16]([C:17]3[CH:18]=[CH:19][C:20]([F:23])=[CH:21][CH:22]=3)[CH2:15][NH:14][C:13]2=[O:24])[CH2:11][CH2:10]1)=[O:5])(=[O:34])[CH3:33]

Participants

5

Reactant 3

HCID 7918Acetic AnhydrideHCID 14923Ammonium HydroxideHCID 21428956HCID 21428956, compound

Product 1

HCID 21428838HCID 21428838, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 9 parts of 2-amino-4-fluoro-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro [4,5]dec-8-yl]ethyl}-benzamide, 8.5 parts of acetic acid anhydride and 85 parts of water is stirred for 30 minutes in a water-bath at about 80° C. The reaction mixture is cooled and alkalized with ammonium hydroxide. The product is extracted with trichloromethane. The aqueous phase is separated and extracted with trichloromethane. The combined organic phases are washed three times with water, dried, filtered and evaporated. The residue is crystallized from 2-propanol. The product is filtered off and dried, yielding 5.2 parts of 2-(acetylamino)-4-fluoro-N-{2-[1-(4-fluorophenyl)-4-oxo-1,3,8-triazaspiro-[4,5]dec-8-yl]ethyl}benzamide; mp. 195.1° C.

Workup

  1. temperatureThe reaction mixture is cooled
  2. extractionThe product is extracted with trichloromethane
  3. customThe aqueous phase is separated
  4. extractionextracted with trichloromethane
  5. washThe combined organic phases are washed three times with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue is crystallized from 2-propanol
  10. filtrationThe product is filtered off
  11. customdried

Sources & evidence

ORD record
ord-9c012fbcba10462e81db522f563a513b
Source dataset
uspto-grants-1977_06
Patent number
US04031226

Reaction notes

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