Carbon Disulfide → HCID 15294893, compound

HRID 1707973Notes

Reaction equation

HRID 1707973 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:9]([C:18]([CH3:21])([CH3:20])[CH3:19])[N:8]=[C:7]([C:22](=[S:24])[NH2:23])[N:6]=1)([CH3:4])[CH3:3].[NH2:25]N.[C:27](=[S:29])=S>CO.O>[CH3:19][C:18]([C:9]1[C:10]([O:11][CH2:12][O:13][CH2:14][CH2:15][O:16][CH3:17])=[C:5]([C:2]([CH3:1])([CH3:3])[CH3:4])[N:6]=[C:7]([C:22]2[S:24][C:27](=[S:29])[NH:25][N:23]=2)[N:8]=1)([CH3:21])[CH3:20]

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 9321HydrazineHCID 19922983HCID 19922983, compound

Product 1

HCID 15294893HCID 15294893, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 962WaterSolvent

Conditions

Temperature
0 °C

Procedure

4,6-Bis(1,1-dimethylethyl)-5-[(2-methoxyethoxy)-methoxy]-2-pyrimidinecarbothioamide (0.22 g, 0.6 mmoles) is dissolved in 5 mL of methanol and added dropwise to 10 mL of 5% hydrazine in methanol at 0° C.. The reaction mixture is stirred at 0° C. for 1 hour, and then diluted with 20 mL of water. The methanol is evaporated under reduced pressure, and the organics are extracted into 50 mL of ethyl acetate. The ethyl acetate extract is washed with brine (4×50 mL) and dried over magnesium sulfate. The solvent is evaporated and the crude amidrazone is dissolved in 10 mL of methanol. Carbon disulfide (0.23 g, 3.1 moles) is added at room temperature. After 10 minutes, the methanol is evaporated and the remaining oil is adsorbed onto a silica gel pad. The pad is eluted with 50% ether/hexane. Evaporation of the eluant gives 0.18 g (73%) of 5-[4,6-bis (1,1-dimethylethyl) -5-[(2-methoxyethoxy) methoxy]-2-pyrimidinyl]-1,3,4-thiadiazole-2 (3H)-thione as an oil. This product is used without further purification in the deprotection reaction.

Workup

  1. customThe methanol is evaporated under reduced pressure
  2. extractionthe organics are extracted into 50 mL of ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washis washed with brine (4×50 mL)
  5. dry with materialdried over magnesium sulfate
  6. customThe solvent is evaporated
  7. dissolutionthe crude amidrazone is dissolved in 10 mL of methanol
  8. waitAfter 10 minutes
  9. customthe methanol is evaporated
  10. washThe pad is eluted with 50% ether/hexane
  11. customEvaporation of the eluant

Sources & evidence

ORD record
ord-14809bd5a5c84493841bbc7eca555f60
Source dataset
uspto-grants-1994_10
Patent number
US05356898

Reaction notes

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