Methanethiol → HCID 73867527, compound

HRID 1032055Notes

Reaction equation

HRID 1032055 reaction equation
[NH:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1.[F:7][B-:8]([F:11])([F:10])[F:9].[CH:12](=[N:19][N+:20]1[CH:24]=[CH:23][N:22]([N:25]=[CH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]=1SC)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1.CS.C(OCC)C>CN(C)C=O>[F:7][B-:8]([F:11])([F:10])[F:9].[CH:12](=[N:19][N+:20]1[CH:24]=[CH:23][N:22]([N:25]=[CH:26][C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[C:21]=1[N:1]1[CH2:6][CH2:5][O:4][CH2:3][CH2:2]1)[C:13]1[CH:14]=[CH:15][CH:16]=[CH:17][CH:18]=1

Participants

6

Reactant 4

HCID 878Methanethiol2×HCID 3283Diethyl EtherHCID 8083MorpholineHCID 73867529HCID 73867529, compound

Product 1

HCID 73867527HCID 73867527, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

1.45 g of absolute morpholine are added under an argon atmosphere to 4.1 g of 1,3-bis-(benzylideneamino)-2-(methylthio)imidazolium tetrafluoroborate in 15 ml of absolute dimethylformamide, whereby the evolution of methyl mercaptan occurs immediately and a yellow-orange solution results. The solution is stirred at room temperature until the cleavage of methyl mercaptan is complete (about 12 hours). Then the solution is treated with 120 ml of diethyl ether and the resulting, slightly yellowish precipitate is removed by filtration under suction. The precipitate is washed five times with diethyl ether, and twice with a small amount of cold ethanol and re-precipitated from acetonitrile/diethyl ether. There is obtained colorless 1,3-bis(benzylideneamino)-2-morpholinoimidazolium tetrafluoroborate of melting point 242°-245° (decomposition).

Workup

  1. customa yellow-orange solution results
  2. custom(about 12 hours)
  3. customthe resulting, slightly yellowish precipitate is removed by filtration under suction
  4. washThe precipitate is washed five times with diethyl ether
  5. customtwice with a small amount of cold ethanol and re-precipitated from acetonitrile/diethyl ether

Sources & evidence

ORD record
ord-4cf8fdf7bbe342d8b34ae7256b056602
Source dataset
uspto-grants-1990_09
Patent number
US04956470

Reaction notes

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