Dimethylformamide → 7-Fluoro-3-methylquinazoline-2,4(1H,3H)-dione

HRID 255300Notes

Reaction equation

HRID 255300 reaction equation
[H-].[Na+].[NH2:3][C:4]1[CH:13]=[C:12]([F:14])[CH:11]=[CH:10][C:5]=1C(NC)=O.ClC(OC1C=CC=CC=1)=[O:17].[CH3:25][N:26]([CH3:29])[CH:27]=[O:28]>>[F:14][C:12]1[CH:13]=[C:4]2[C:5]([C:27](=[O:28])[N:26]([CH3:29])[C:25](=[O:17])[NH:3]2)=[CH:10][CH:11]=1

Participants

5

Reactant 4

HCID 6228DimethylformamideHCID 15891Phenyl chloroformate2×HCID 24758Sodium hydrideHCID 569516612-amino-4-fluoro-N-methylbenzamide2×

Product 1

HCID 667752467-Fluoro-3-methylquinazoline-2,4(1H,3H)-dioneYield 51%

Conditions

Temperature
0 °C

Procedure

A suspension of sodium hydride (60% in mineral oil, 368 mg, 9.2 mmol) in dimethylformamide (12 mL) was cooled to 0° C. and treated with 2-amino-4-fluoro-N-methylbenzamide [Intermediate 137] (0.67 g, 4.0 mmol). Phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added over 40 minutes. After 1 hour a further portion of phenyl chloroformate (0.6 mL, 0.73 g, 4.7 mmol) was added. The reaction was allowed to warm to room temperature and stir for two hours. The reaction was slowly added to 200 mL of ice. The solid was filtered, washed with methanol to obtain the product (395 mg, 51%).

Workup

  1. temperatureto warm to room temperature
  2. filtrationThe solid was filtered
  3. washwashed with methanol

Sources & evidence

ORD record
ord-cb091bfb885a412b994ba73e7dcf7efe
Source dataset
uspto-grants-2011_01
Patent number
US07875715B2

Reaction notes

Loading…