Hydrochloric Acid → HCID 178519764, compound

HRID 2185190Notes

Reaction equation

HRID 2185190 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]4OCC[O:25]4)[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].Cl>O1CCCC1.CS(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]2[N:19]=[C:18]([OH:20])[C:17]3[C:12](=[C:13]([CH:24]=[O:25])[CH:14]=[C:15]([N+:21]([O-:23])=[O:22])[CH:16]=3)[N:11]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

Participants

5

Reactant 2

HCID 313Hydrochloric AcidHCID 178526503HCID 178526503, compound

Product 1

HCID 178519764HCID 178519764, compoundYield 103.4%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
40 °C

Procedure

A solution 2-((3,4-dichlorophenyl)amino)-8-(1,3-dioxolan-2-yl)-6-nitroquinazolin-4-ol (1.08 g) in tetrahydrofuran (35 mL) and dimethylsulfoxide (1 mL) was treated with 10% (v/v) hydrochloric acid (25 mL). The resulting mixture was stirred at 40° C. for 7 h, then was cooled to room temperature and stirred for 16 h. Evaporation of the tetrahydrofuran in vacuo provided a brown slurry, from which the product was isolated by filtration. The brown solids were washed with water (50 mL) and dried. The crude product was dissolved in tetrahydrofuran (3.75 mL), dried over MgSO4, filtered and evaporated to afford the title compound (1.0 g) as a yellow solid. 1H NMR (300 MHz, DMSO-d6): 10.57 (s, 1H), 8.72 (d, J=2.7 Hz, 1H), 8.54 (bd, J=2.1 Hz, 1H), 8.03 (bd, J=2.1 Hz, 1H), 7.56 (d, J=8.7 Hz, 1H), 7.49 (dd, J=2.1, 8.7 Hz, 1H). HPLC Method A: 7.73 min. MS (APCI−): m/z 377, 379.

Workup

  1. temperaturewas cooled to room temperature
  2. stirringstirred for 16 h
  3. customEvaporation of the tetrahydrofuran in vacuo
  4. customprovided a brown slurry
  5. customfrom which the product was isolated by filtration
  6. washThe brown solids were washed with water (50 mL)
  7. customdried
  8. dissolutionThe crude product was dissolved in tetrahydrofuran (3.75 mL)
  9. dry with materialdried over MgSO4
  10. filtrationfiltered
  11. customevaporated

Sources & evidence

ORD record
ord-85770270495a4b2ead504d5985455ed5
Source dataset
uspto-grants-2002_06
Patent number
US06399603B1

Reaction notes

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