1,1'-Carbonyldiimidazole → HCID 21644871, compound

HRID 2356848Notes

Reaction equation

HRID 2356848 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([OH:12])=O)[CH:5]=[C:6]([F:8])[CH:7]=1.C(N1C=CN=C1)([N:15]1C=CN=C1)=O>O1CCCC1>[F:1][C:2]1[CH:3]=[C:4]([CH2:9][C:10]([NH2:15])=[O:12])[CH:5]=[C:6]([F:8])[CH:7]=1

Participants

4

Reactant 2

HCID 682631,1'-CarbonyldiimidazoleHCID 1454243,5-Difluorophenylacetic acid

Product 1

HCID 21644871HCID 21644871, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
25 °C

Procedure

A solution of 10 g of (3,5-difluorophenyl)acetic acid in 100 mL of tetrahydrofuran was treated with 9.9 g of carbonyldiimidazole. The mixture was stirred at 25° C. for 3 hours then a vigorous stream of anhydrous ammonia was bubbled through the solution for 1 hour. The mixture was stirred for 2 days and then the solvent was evaporated at reduced pressure. The residue was suspended in 100 mL of distilled water. The mixture was filtered and the filtrant washed with distilled water twice. After drying in a stream of air, the (3,5-difluorophenyl)acetamide was obtained as 8.4 g of an ivory solid. 1H-NMR (DMSO-d6): δ 7.51 (broad s, 1H), 7.15-6.85 (m, 3H), 3.40 (s, 2H). MS (EI): m/z 171. EA Calc'd for C—8H7NO: C, 56.13; H, 4.13; N, 8.18. Found: C, 56.16; H, 4.05; N, 8.07.

Workup

  1. customa vigorous stream of anhydrous ammonia was bubbled through the solution for 1 hour
  2. stirringThe mixture was stirred for 2 days
  3. customthe solvent was evaporated at reduced pressure
  4. filtrationThe mixture was filtered
  5. washthe filtrant washed with distilled water twice
  6. customAfter drying in a stream of air

Sources & evidence

ORD record
ord-9ab4383a61ee42bb98b417275162bdf5
Source dataset
uspto-grants-2010_07
Patent number
US07759382B2

Reaction notes

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