Ethanol → HCID 135708792, compound

HRID 369803Notes

Reaction equation

HRID 369803 reaction equation
[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([CH3:25])[C:15]3[S:19][C:18]([C:20]([O:22]CC)=[O:21])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=1.CCO.[OH-].[Na+]>C(Cl)Cl>[CH3:1][C:2]1[NH:11][C:10](=[O:12])[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([CH2:13][N:14]([CH3:25])[C:15]3[S:19][C:18]([C:20]([OH:22])=[O:21])=[CH:17][CH:16]=3)[CH:8]=2)[N:3]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14798Sodium HydroxideHCID 135836106HCID 135836106, compound

Product 1

HCID 135708792HCID 135708792, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 25 mL 3-necked flask equipped with a condenser, a thermometer, and a magnetic stirrer was charged with 0.20 g of ethyl 5-(((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thiophene-carboxylate, 6 mL of EtOH, and 6 mL of 1N aqueous NaOH. The resulting solution was stirred under nitrogen and RT for 25 min and then at 55° C. for 2 h. Analysis by tlc (SiO2, 95:5 CH2Cl2) indicated no remaining starting material and a new component at Rf =0.06. The solution was cooled to RT and subjected to rotary evaporation to remove EtOH. The remaining solution was diluted with 10 mL of water and acidified to pH=3.5 by addition of 1N aqueous HCl. A tan precipitate formed which was collected by centrifugation, washed with four cycles of aqueous suspension-centrifugation-decantation, and lyophilized to afford 0.116 g (63%) of 5-(((3,4-dihydro-2-methyl-4-oxo-6-quinazolinyl)methyl)methylamino)-2-thiophene-carboxylic acid as a white powder, m.p. 195° C. (dec).

Workup

  1. customA 25 mL 3-necked flask equipped with a condenser
  2. waitat 55° C. for 2 h
  3. temperatureThe solution was cooled to RT
  4. customsubjected to rotary evaporation
  5. customto remove EtOH
  6. additionThe remaining solution was diluted with 10 mL of water
  7. additionacidified to pH=3.5 by addition of 1N aqueous HCl
  8. customA tan precipitate formed which
  9. customwas collected by centrifugation
  10. washwashed with four cycles of aqueous suspension-centrifugation-decantation

Sources & evidence

ORD record
ord-b9b58bc86126453190a9e2fbb59bb0be
Source dataset
uspto-grants-2000_10
Patent number
US06140100

Reaction notes

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