Methanethiol → HCID 73867527, compound

HRID 1165153Notes

Reaction equation

HRID 1165153 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH:6](=[N:13][N+:14]1[CH:18]=[CH:17][N:16]([N:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1SC)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[NH:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1.CS>C(#N)C>[F:1][B-:2]([F:5])([F:4])[F:3].[CH:6](=[N:13][N+:14]1[CH:18]=[CH:17][N:16]([N:19]=[CH:20][C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[C:15]=1[N:29]1[CH2:34][CH2:33][O:32][CH2:31][CH2:30]1)[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1

Participants

5

Reactant 3

HCID 878Methanethiol2×HCID 8083MorpholineHCID 73867529HCID 73867529, compound

Product 1

HCID 73867527HCID 73867527, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

4.1 g of 1,3-bis(benzylideneamino)-2-(methylthio)imidazolium tetrafluoroborate in 25 ml of absolute acetonitrile are treated under an argon atmosphere with 1.45 g of absolute morpholine, whereby the evolution of methylmercaptan sets in immediately and solution occurs. The solution is left to stir overnight at room temperature until the cleavage of methylmercaptan is complete. The resulting colorless precipitate is removed by filtration. The filtrate is treated with 30 ml of diethyl ether and again filtered. The two filter residues are combined and reprecipitated from acetonitrile/ether. There is obtained 1,3-bis(benzylideneamino)-2-morpholinoimidazolium tetrafluoroborate in the form of colorless crystals of m.p. 244°-247° (dec.).

Workup

  1. waitThe solution is left
  2. customThe resulting colorless precipitate is removed by filtration
  3. additionThe filtrate is treated with 30 ml of diethyl ether
  4. filtrationagain filtered
  5. filtrationThe two filter residues
  6. customreprecipitated from acetonitrile/ether

Sources & evidence

ORD record
ord-c2176249c50b415596fe020bc956e950
Source dataset
uspto-grants-1990_03
Patent number
US04908363

Reaction notes

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