Sodium methanethiolate → HCID 178503807, compound

HRID 1977223Notes

Reaction equation

HRID 1977223 reaction equation
[CH3:1][S-:2].[Na+].Br[CH2:5][CH2:6][N:7]1[C:20](=[O:21])[C:19]2[C:18](=[O:22])[C:17]3[CH:16]=[CH:15][C:14]([Cl:23])=[CH:13][C:12]=3[NH:11][C:10]=2[C:9]([OH:24])=[N:8]1>CN(C)C=O>[Cl:23][C:14]1[CH:15]=[CH:16][C:17]2[C:18](=[O:22])[C:19]3[C:20](=[O:21])[N:7]([CH2:6][CH2:5][S:2][CH3:1])[N:8]=[C:9]([OH:24])[C:10]=3[NH:11][C:12]=2[CH:13]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 178515080HCID 178515080, compound

Product 1

HCID 178503807HCID 178503807, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of sodium thiomethoxide (230 mg, 3.2 mM) in dimethylformamide (20 mL), was added in one portion 2-(2-bromoethyl)-7-chloro-4-hydroxy-1,2,5,10-tetrahydropyridazino[4,5-b]quinoline-1,10-dione (0.4 g, 1.08 mM, prepared in Example 4a. of docket No. 37811) as a dry powder. This mixture was warmed to gentle reflux for about three hours. At this point the heat was removed and the reaction mixture was poured into ice cold 1.2N HCl (100 mL) and stirred about one hour. The resulting precipitate was vacuum filtered and washed with water and ether, then vacuum dried at 50° C. to yield 330 mg (91%) of the title compound as an off white powder. mp=275-277° C.; MS: 338(H+1).

Workup

  1. customprepared in Example 4a
  2. temperatureThis mixture was warmed
  3. temperatureto gentle reflux for about three hours
  4. customAt this point the heat was removed
  5. additionthe reaction mixture was poured into ice cold 1.2N HCl (100 mL)
  6. filtrationfiltered
  7. washwashed with water and ether
  8. customvacuum dried at 50° C.

Sources & evidence

ORD record
ord-85a83e0057784cc6a9468b7cb2d1a29e
Source dataset
uspto-grants-2001_05
Patent number
US06232313B1

Reaction notes

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