4-Aminobenzophenone → N-[4-(Phenylcarbonyl)phenyl]-3,3-difluoro-2-hydroxy-2-difluoromethylpropanamide

HRID 1769792Notes

Reaction equation

HRID 1769792 reaction equation
[F:1][CH:2]([F:11])[C:3]([CH:8]([F:10])[F:9])([OH:7])[C:4](O)=[O:5].C(C1NC=CN=1)(C1NC=CN=1)=O.[NH2:24][C:25]1[CH:38]=[CH:37][C:28]([C:29]([C:31]2[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=2)=[O:30])=[CH:27][CH:26]=1>O1CCCC1>[C:31]1([C:29]([C:28]2[CH:27]=[CH:26][C:25]([NH:24][C:4](=[O:5])[C:3]([OH:7])([CH:8]([F:10])[F:9])[CH:2]([F:11])[F:1])=[CH:38][CH:37]=2)=[O:30])[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=1

Participants

5

Reactant 3

HCID 143464-AminobenzophenoneHCID 5250894Bis-(1H-imidazol-2-YL)-methanoneHCID 222874542,2-Bis-difluoromethyl-2-hydroxyacetic acid

Product 1

HCID 21480127N-[4-(Phenylcarbonyl)phenyl]-3,3-difluoro-2-hydroxy-2-difluoromethylpropanamideYield 25%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,2,-bis-difluoromethyl-2-hydroxy-acetic acid (1.76 g, 10 mmole) in tetrahydrofuran(40 ml) was added carbonyl diimidazole (0.81 g, 5 mmole). The flask was placed in a sonic bath and the reaction sonicated for 20 minutes followed by addition of 4-aminobenzophenone. The reaction was sonicated for 18 hours. The reaction mixture was filtered and the filtrate evaporated to dryness. The recovered pasty solid was washed with ether and the combined ether washings evaporated. The recovered solid was crystallized from ethyl acetate/hexane to give the title compound (0.89 g, 25%) as yellow crystals; mp 139°-142° C. 1H-NMR (300 MHz, d6 -DMSO): 6.48(t, J=53.7 Hz, 2H, HCF2); 7.53-7.77 (m, 7H, ArH, OH); 7.95-7.98 (m, 3H, ArH); 10.43 (s, 1H, NH). MS(CI,CH4): 356 (M+1, 100%).

Workup

  1. customThe flask was placed in a sonic bath
  2. customthe reaction sonicated for 20 minutes
  3. customThe reaction was sonicated for 18 hours
  4. filtrationThe reaction mixture was filtered
  5. customthe filtrate evaporated to dryness
  6. washThe recovered pasty solid was washed with ether
  7. customthe combined ether washings evaporated
  8. customThe recovered solid was crystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-55d7ece429f340f99627035e59bc4b57
Source dataset
uspto-grants-1995_01
Patent number
US05382598

Reaction notes

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