Dichloromethane → HCID 90412148, compound

HRID 717353Notes

Reaction equation

HRID 717353 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:13]2[N:22]=[C:21](O)[C:20]3[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=3)[N:14]=2)[CH:6]=[C:7]([O:11][CH3:12])[C:8]=1[O:9][CH3:10].[Cl:24]CCl.C(Cl)(C(Cl)=O)=O>CN(C)C=O>[Cl:24][C:21]1[C:20]2[C:15](=[CH:16][CH:17]=[CH:18][CH:19]=2)[N:14]=[C:13]([C:5]2[CH:4]=[C:3]([O:2][CH3:1])[C:8]([O:9][CH3:10])=[C:7]([O:11][CH3:12])[CH:6]=2)[N:22]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 65578Oxalyl chlorideHCID 178488018HCID 178488018, compound

Product 1

HCID 90412148HCID 90412148, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Into a 1-L 3-necked round-bottom flask, was placed 2-(3,4,5-trimethoxyphenyl)quinazolin-4-ol (12 g, 38.5 mmol, 1.00 equiv), dichloromethane (500 mL) and N,N-dimethylformamide (0.5 mL). This was followed by the addition of (COCl)2 (15 g) dropwise with stirring at 0° C. The resulting solution was heated to reflux for 1 h in an oil bath. The reaction was then quenched by the addition of 50 mL of sodium bicarbonate (sat.). The resulting solution was extracted with 2×100 mL of dichloromethane and the organic layers combined. The mixture was dried over anhydrous sodium sulfate and concentrated under vacuum. The residue was applied onto a silica gel column with ethyl acetate:dichloromethane:petroleum ether (1:1:4). This resulted in 10 g (78.7%) of 4-chloro-2-(3,4,5-trimethoxyphenyl)quinazoline as a white solid. MS (ESI) m/z 332 ([M+H]+).

Workup

  1. customInto a 1-L 3-necked round-bottom flask, was placed
  2. temperatureThe resulting solution was heated
  3. temperatureto reflux for 1 h in an oil bath
  4. customThe reaction was then quenched by the addition of 50 mL of sodium bicarbonate (sat.)
  5. extractionThe resulting solution was extracted with 2×100 mL of dichloromethane
  6. dry with materialThe mixture was dried over anhydrous sodium sulfate
  7. concentrationconcentrated under vacuum
  8. customThis resulted in 10 g (78.7%) of 4-chloro-2-(3,4,5-trimethoxyphenyl)quinazoline as a white solid

Sources & evidence

ORD record
ord-0b2e54c32cee469d9a098bc731cf66e9
Source dataset
uspto-grants-2015_11
Patent number
US09193707B2

Reaction notes

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