Dimethylformamide → HCID 23505628, compound

HRID 1884390Notes

Reaction equation

HRID 1884390 reaction equation
Cl[CH2:2][C:3]1[N+:12]([O-:13])=[C:11]([C:14]2[CH:19]=[CH:18][C:17]3[O:20][CH2:21][O:22][C:16]=3[CH:15]=2)[C:10]2[C:5](=[CH:6][C:7]3[O:25][CH2:24][O:23][C:8]=3[CH:9]=2)[N:4]=1.[NH:26]1[CH2:30][CH2:29][CH2:28][CH2:27]1.CN(C=O)C>CO>[N:26]1([CH2:2][C:3]2[N+:12]([O-:13])=[C:11]([C:14]3[CH:19]=[CH:18][C:17]4[O:20][CH2:21][O:22][C:16]=4[CH:15]=3)[C:10]3[C:5](=[CH:6][C:7]4[O:25][CH2:24][O:23][C:8]=4[CH:9]=3)[N:4]=2)[CH2:30][CH2:29][CH2:28][CH2:27]1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 31268PyrrolidineHCID 23505617HCID 23505617, compound

Product 1

HCID 23505628HCID 23505628, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
65 °C

Procedure

To a suspension of 2-chloromethyl-6,7-methylenedioxy-4-(3,4-methylenedioxyphenyl)quinazoline-3-oxide (200 mg, 0.55 mmol), in MeOH (5 mL), was added pyrrolidine (0.4 mL). The mixture was stirred at 65° C. for 1.5 h. DMF (6 mL) was added and the heating was continued at 60° C. for 15 h. After cooling, the separated solid was collected by filtration, washed with hexane, and air dried to give the title compound as off white solid (175 mg). The crude product was purified by column chromatography on silica gel (CH2Cl2:MeOH 95:5); mp 194-202° C. 1H NMR (CDCl3) 7.39 (s, 1H), 6.90-7.06 (m, 4H), 6.78 (s 1H), 6.11 (s, 2H), 6.08 (s, 2H), 4.25 (s, 2H), 2.87 (bs, 4H), 1.91 (bs, 4H).

Workup

  1. waitthe heating was continued at 60° C. for 15 h
  2. temperatureAfter cooling
  3. filtrationthe separated solid was collected by filtration
  4. washwashed with hexane, and air
  5. customdried

Sources & evidence

ORD record
ord-37c3611fe5c1402abb8ffe50f1601de0
Source dataset
uspto-grants-2004_07
Patent number
US06765006B2

Reaction notes

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