Sodium Hydroxide → HCID 86639524, compound

HRID 1022403Notes

Reaction equation

HRID 1022403 reaction equation
C([S:4][CH2:5][CH2:6][NH:7][C:8]1[N:17]=[C:16]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:15]2[C:10](=[CH:11][CH:12]=[C:13]([Cl:24])[CH:14]=2)[N:9]=1)(=O)C.[OH-].[Na+]>C(O)C>[Cl:24][C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[N:9]=[C:8]([NH:7][CH2:6][CH2:5][SH:4])[N:17]=[C:16]2[C:18]1[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=1

Participants

4

Reactant 2

HCID 14798Sodium HydroxideHCID 86639523HCID 86639523, compound

Product 1

HCID 86639524HCID 86639524, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 108 ma of 2-(2-acetylthioethylamino)-6-chloro-4-phenylquinazoline (compound No. Ic3-14), 2 ml of ethanol and 362 mg of an aqueous 10% sodium hydroxide solution was stirred at room temperature for 2 hours and stirred under heating under reflux for 30 minutes. Then insoluble substances were collected by filtration from the reaction solution. The collected product (solid) was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1) to obtain 50 mg of 6-chloro-2-(2-mercaptoethylamino)-4-phenylquinazoline, first. Mp.165.9° C. 1H NMR (CDCl3): 1.46 (1H, t, J=8.5 Hz), 2.84 (2H, q-like, J=7.2 Hz), 3.66 (2H, q-like, J=6.4 Hz), 5.79 (1H, br. t, J=5.4 Hz), 7.55-7.57 (3H, m), 7.60 (2H, s), 7.66-7.69 (2H, m), 7.77-7.78 (1H, m). Then, 28 mg of bis[2-(6-chloro-4-phenyl-2-quinazolinyl)aminoethyl]disulfide (compound represented by the following formula) was obtained.

Workup

  1. temperatureunder heating
  2. temperatureunder reflux for 30 minutes
  3. filtrationThen insoluble substances were collected by filtration from the reaction solution
  4. customThe collected product (solid) was purified by silica gel column chromatography (chloroform:ethyl acetate=10:1)

Sources & evidence

ORD record
ord-211f0be4820448138f2b061be27e9969
Source dataset
uspto-grants-2014_05
Patent number
US08722580B2

Reaction notes

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