Diethyl Ether → HCID 178503974, compound

HRID 2379461Notes

Reaction equation

HRID 2379461 reaction equation
[C:1]1([NH:7][C:8]([NH2:10])=[S:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[I:12].[CH2:13](OCC)C>C(O)C>[IH:12].[C:1]1([NH:7][C:8]([S:9][CH3:13])=[NH:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 6328Methyl iodideHCID 676454Phenylthiourea

Product 1

HCID 178503974HCID 178503974, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a stirred, chilled (+3° C.) suspension of phenyl-thiourea (15.66 g, 0.1029 mol) in absolute ethanol under nitrogen atmosphere was added in one portion methyl iodide (6.4 mL, 0.10 mol), and the mixture was stirred for 1.5 hours. The suspension was allowed to warm to room temperature over 1.5 hours and was stirred. All of the solids dissolved within 5 hours at room temperature to give a yellow solution. After 6 hours a thick off-white precipitate formed. After 40 hours diethyl ether (400 mL) was added dropwise. The solids were filtered off, washed with diethyl ether, and dried in vacuo (25° C.), yield 28.26 g (97%), mp=142°-144° C.

Workup

  1. temperatureTo a stirred, chilled
  2. stirringwas stirred
  3. dissolutionAll of the solids dissolved within 5 hours at room temperature
  4. customto give a yellow solution
  5. customAfter 6 hours a thick off-white precipitate formed
  6. filtrationThe solids were filtered off
  7. washwashed with diethyl ether
  8. customdried in vacuo (25° C.), yield 28.26 g (97%), mp=142°-144° C.

Sources & evidence

ORD record
ord-b5f795a01af94caeb999991f909f6d0d
Source dataset
uspto-grants-1994_11
Patent number
US05362744

Reaction notes

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