Benzoyl chloride → 2-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)acetic acid

HRID 2099604Notes

Reaction equation

HRID 2099604 reaction equation
[N:1]1([CH2:9][C:10]([O:12]C(=O)C2C=CC=CC=2)=[O:11])[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[O:3].[C:21](Cl)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1>N1C=CC=CC=1>[C:21]([NH:6][C:5]1[CH:7]=[CH:8][N:1]([CH2:9][C:10]([OH:12])=[O:11])[C:2](=[O:3])[N:4]=1)(=[O:28])[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

4

Reactant 2

HCID 7412Benzoyl chlorideHCID 53946337Benzoyl cytosin-1-ylacetate

Product 1

HCID 153419782-(4-Benzamido-2-oxopyrimidin-1(2H)-yl)acetic acid

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of (1) (10 g, 38 mmol) in 10 mL pyridine was added 6.6 g (47 mmol) of benzoyl chloride and stirred overnight at room temperature. The solution was evaporated under reduced pressure. The residue was dissolved in 1 M KOH and stirred for 3 h after which the Ph was adjusted to 2 with conc. HCl. The target compound (2) precipitated out. Yield: 9.3 g (90%). 1H NMR (d6-DMSO): δ 4.59 (s, 2H, CH2O), 7.31 (d, 1H, H5), 7.5-8.2 (7H, aromatic, NH, H6). MS (FAB) m/z 273 (M+H)+ (calcd 273).

Workup

  1. customThe solution was evaporated under reduced pressure
  2. dissolutionThe residue was dissolved in 1 M KOH
  3. stirringstirred for 3 h after which the Ph
  4. customThe target compound (2) precipitated out

Sources & evidence

ORD record
ord-7810038e52df4a1284cbf69a8e4bcb6f
Source dataset
uspto-grants-2009_08
Patent number
US07569659B1

Reaction notes

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