Methyl iodide → HCID 54516938, compound

HRID 1164683Notes

Reaction equation

HRID 1164683 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([O:9][CH3:10])[N:6]=[C:5]([NH:11][C:12]([NH:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=2[C:28]([O:30][CH3:31])=[O:29])(=[O:17])=[O:16])=[S:13])[N:4]=1.O([CH3:34])[Na].CO.CI>O1CCCC1>[CH3:10][O:9][C:7]1[CH:8]=[C:3]([O:2][CH3:1])[N:4]=[C:5]([NH:11][C:12](=[N:14][S:15]([C:18]2[C:27]3[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=3)[CH:21]=[CH:20][C:19]=2[C:28]([O:30][CH3:31])=[O:29])(=[O:17])=[O:16])[S:13][CH3:34])[N:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 86738759HCID 86738759, compoundHCID 178501943HCID 178501943, compound

Product 1

HCID 54516938HCID 54516938, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a suspension of methyl 1-[[(4,6-dimethoxypyrimidin-2-yl)aminothiocarbonyl]aminosulfonyl]-2-naphthalenecarboxylate in 200 ml of anhydrous tetrahydrofuran can be added 16.7 ml of 3 M NaOCH3 /MeOH solution. The resulting reaction mixture can be heated to reflux, 3.1 ml of methyl iodide in 10 ml of anhydrous tetrahydrofuran can be added; and the reaction mixture can be refluxed for 3 hours. The reaction mixture can be cooled to cause the formation of a precipitate which can be filtered off and washed with tetrahydrofuran to afford the desired product.

Workup

  1. customThe resulting reaction mixture
  2. temperaturecan be heated
  3. temperatureto reflux
  4. temperatureand the reaction mixture can be refluxed for 3 hours
  5. temperatureThe reaction mixture can be cooled
  6. filtrationcan be filtered off
  7. washwashed with tetrahydrofuran

Sources & evidence

ORD record
ord-568478ef52844844a098996a06538f15
Source dataset
uspto-grants-1983_01
Patent number
US04370479

Reaction notes

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