Thionyl Chloride → HCID 178505705, compound

HRID 717325Notes

Reaction equation

HRID 717325 reaction equation
[F:1][C:2]1[CH:16]=[CH:15][C:5]([C:6]([NH:8][C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=O)=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>>[F:1][C:2]1[CH:16]=[CH:15][C:5](/[C:6](/[Cl:19])=[N:8]/[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=2)=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 960954-Fluorobenzanilide

Product 1

HCID 178505705HCID 178505705, compound

Procedure

Into a 500-mL 3-necked round-bottom flask, was placed 4-fluoro-N-phenylbenzamide (50 g; 233 mmol) and thionyl chloride (200 mL). The mixture was stirred at refluxed for 3 h and then the solvent was evaporated to dryness to afford (Z)-4-fluoro-N-phenylbenzimidoyl chloride as white solid. The solid was dissolved into chlorobenzene and SnCl4 (39.0 mmol) and ethyl cyanoformate (39.0 mmol) were added. The reaction mixture was heated at 140° C. for 1 hour and concentrated to get black oil. The black oil was added into water, made alkaline with 20% NaOH, and extracted with 2×300 mL of dichloromethane. The organic layer was washed with 1×100 mL of brine and dried over sodium sulphate and concentrated to get the crude product, which was purified by flash chromatography on silica gel, eluting with hexane/ethyl acetate (10:1) to afford ethyl 2-(4-fluorophenyl)quinazoline-4-carboxylate as white solid (8.1 g, 11.7%, 2 steps). MS (ESI) m/z 297 ([M+H]+).

Workup

  1. customInto a 500-mL 3-necked round-bottom flask, was placed
  2. temperatureat refluxed for 3 h
  3. customthe solvent was evaporated to dryness

Sources & evidence

ORD record
ord-445eef8af6124cd58339b1e2432cce55
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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