Ethanol → HCID 19363223, compound

HRID 850508Notes

Reaction equation

HRID 850508 reaction equation
[NH2:1][C:2]1[C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:20]([O:28][CH3:29])[CH:19]=[CH:18][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=1)=[O:5].C(N(CC)CC)C.Cl[C:38](Cl)([O:40]C(=O)OC(Cl)(Cl)Cl)Cl.C(O)C>C(Cl)(Cl)Cl>[CH3:29][O:28][C:20]1[C:21]([O:22][CH2:23][CH2:24][CH2:25][CH2:26][CH3:27])=[C:2]2[C:3]([C:4](=[O:5])[N:6]([CH2:7][CH2:8][C:9]3[CH:14]=[CH:13][C:12]([N+:15]([O-:17])=[O:16])=[CH:11][CH:10]=3)[C:38](=[O:40])[NH:1]2)=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 94429TriphosgeneHCID 19363465HCID 19363465, compound

Product 1

HCID 19363223HCID 19363223, compoundYield 183.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Conditions

Temperature
50 °C

Procedure

2-Amino-4-methoxy-N-[2-(4-nitrophenyl)ethyl]-3-pentyloxybenzamide (15.0 g, 37.4 mmol) obtained in Example 2-46, triethylamine (5.30 ml, 38.0 mmol) and chloroform (200 ml) were mixed, and a solution (10 ml) of triphosgene (4.75 g, 16.0 mmol) in chloroform was added dropwise to this solution. After stirring at 50° C. for 11.5 hours, ethanol (20 ml) was added to stop the reaction. The organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution (100 ml, 50 ml) and water (100 ml, 50 ml). This solution was dried over anhydrous magnesium sulfate, and the drying agent was filtered off. The filtrate was concentrated under reduced pressure. A hexane-chloroform solution (10:1, 110 ml) was added to the precipitated crystals, and the crystals were washed by stirring to give 7-methoxy-3-[2-(4-nitrophenyl)ethyl]-8-pentyloxy-1H-quinazoline-2,4-dione (12.56 g, 79%) as pale-yellow crystals.

Workup

  1. customthe reaction
  2. washThe organic layer was washed successively with saturated aqueous sodium hydrogencarbonate solution (100 ml, 50 ml) and water (100 ml, 50 ml)
  3. dry with materialThis solution was dried over anhydrous magnesium sulfate
  4. filtrationthe drying agent was filtered off
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. additionA hexane-chloroform solution (10:1, 110 ml) was added to the precipitated crystals
  7. washthe crystals were washed
  8. stirringby stirring

Sources & evidence

ORD record
ord-7152f46c6c2f40e688db01b23535b730
Source dataset
uspto-grants-2000_01
Patent number
US06017919

Reaction notes

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