Potassium Carbonate → HCID 12150197, compound

HRID 1884381Notes

Reaction equation

HRID 1884381 reaction equation
Cl[CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:24][CH2:23][O:22][C:8]=3[CH:9]=2)[N:4]=1.[SH:25][C:26]1[N:27]([CH3:31])[CH:28]=[CH:29][N:30]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH3:31][N:27]1[CH:28]=[CH:29][N:30]=[C:26]1[S:25][CH2:2][C:3]1[N:12]=[C:11]([C:13]2[CH:18]=[CH:17][C:16]3[O:19][CH2:20][O:21][C:15]=3[CH:14]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:24][CH2:23][O:22][C:8]=3[CH:9]=2)[N:4]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 12150202HCID 12150202, compoundHCID 178480602HCID 178480602, compound

Product 1

HCID 12150197HCID 12150197, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxy-phenyl)quinazoline (193 mg, 0.61 mmol) and 2-mercapto-1-methylimidazole (80 mg, 0.7 mmol) in dry DMF (2 mL) was treated with K2CO3 (97 mg, 0.7 mmol). The mixture was stirred at rt for 2 h, and then it was poured into ice-water. The mixture were extracted with EtOAc and the extract was washed with water and brine, dried over anhydrous MgSO4, and evaporated to yield the crude product, which was crystallized from EtOAc-hexane to give the title compound as colorless rods (142 mg); mp 155-160° C.; 1H NMR (CDCl3) 7.36 (s, 1H), 7.27 (s, 1H), 7.17 (d, J=7.7, 1H), 7.16 (s, 1H), 7.09 (s, 1H), 6.95 (d, J=7.7, 1H), 6.91 (s,13H), 6.14 (s, 2H), 6.07 (s, 2H), 4.53 (s, 2H), 3,51 (s, 3H). Anal. calcd. for C21H16N4O4S: C, 59.99; H 3.84; N 13.33. Found: C, 59.78; H 3.82; N 13.20.

Workup

  1. extractionThe mixture were extracted with EtOAc
  2. washthe extract was washed with water and brine
  3. dry with materialdried over anhydrous MgSO4
  4. customevaporated
  5. customto yield the crude product, which
  6. customwas crystallized from EtOAc-hexane

Sources & evidence

ORD record
ord-b71da18c646d485587288ade62debe86
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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