Sodium methanethiolate → HCID 136360484, compound

HRID 2079618Notes

Reaction equation

HRID 2079618 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][C:9]([NH:13][C:14]3[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)=[N:10]2)=[CH:5][CH:4]=1.C[S-].[Na+]>CN1C(=O)CCC1>[OH:2][C:3]1[CH:12]=[C:11]2[C:6]([CH:7]=[N:8][C:9]([NH:13][C:14]3[CH:15]=[C:16]([S:20]([NH2:23])(=[O:22])=[O:21])[CH:17]=[CH:18][CH:19]=3)=[N:10]2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4378561Sodium methanethiolateHCID 67102012HCID 67102012, compound

Product 1

HCID 136360484HCID 136360484, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
80 °C

Procedure

To a 0.02M solution of 3-(7-Methoxyquinazolin-2-ylamino)benzenesulfonamide in NMP was added sodium thiomethoxide (5.0 eq) at ambient temperature. The reaction was stirred at 80° C. for 3 hours. The solid was collected by vacuum filtration and was partitioned between ethyl acetate and water. Saturated ammonium hydrochloride was added to aqueous phase until the PH=6. Aqueous phase was extracted with ethyl acetate. The organic phase was washed with brine, dried over sodium sulfate and concentrated to give desired product in 85% yield. ES/MS m/z 317 (MH+).

Workup

  1. filtrationThe solid was collected by vacuum filtration
  2. customwas partitioned between ethyl acetate and water
  3. additionSaturated ammonium hydrochloride was added to aqueous phase until the PH=6
  4. extractionAqueous phase was extracted with ethyl acetate
  5. washThe organic phase was washed with brine
  6. dry with materialdried over sodium sulfate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-8762219f6b3b4645b57a1d19431767fc
Source dataset
uspto-grants-2011_04
Patent number
US07932262B2

Reaction notes

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