1,1,3,3-Tetramethyl-2-thiourea → HCID 178433057, compound

HRID 728521Notes

Reaction equation

HRID 728521 reaction equation
[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:6][N:7](C)[C:8](=[S:12])[N:9]([CH3:11])[CH3:10].[CH3:14][N:15](C)[C:16](=[S:20])[N:17]([CH3:19])[CH3:18].[CH3:22][N:23](C)C(=S)N(C)C.[H+].[B-](F)(F)(F)F>O.[Au+]>[F:1][B-:2]([F:5])([F:4])[F:3].[CH3:14][N+:15]1[N:7]=[C:8]([S-:12])[N:9]([CH3:11])[C:10]=1[CH3:22].[CH3:22][N+:23]1[N:15]=[C:16]([S-:20])[N:17]([CH3:19])[C:18]=1[CH3:6]

Participants

6

Reactant 3

HCID 177251,1,3,3-Tetramethyl-2-thioureaHCID 28118Tetrafluoroboric acidHCID 86745055HCID 86745055, compound

Product 1

HCID 178433057HCID 178433057, compoundYield 86%

Reagents, catalysts & solvents 2

HCID 114945Gold(1+)CatalystHCID 962WaterSolvent2×

Conditions

Temperature
60 °C

Procedure

First the gold(I) starting compound, aurous bis(tetramethyl-thiourea) tetrafluoroborate, was made as follows. HAuCl4.3H2O (0.255 g) was dissolved in 5 mL water and added dropwise to tetramethylthiourea (0.327 g) which was partly dissolved in water. Dark orange and red precipitates formed initially, but after stirring at about 50° to 60° C. the precipitates dissolved and the solution became completely clear and colorless. 0.2 mL HBF4 solution (49% aqueous) was added. After cooling a few hours, white platelets of the product were filtered (84% yield). This intermediate gold(I) compound (0.228 g) was dissolved in 4 mL water by heating to about 60° C., and then added to a room temperature solution of 1,4,5-trimethyl-1,2,4-triazolium-3-thiolate (0.126 g). A white precipitate began to form, and was filtered after standing in the refrigerator a few hours. The product yield was 86%. The product could be recrystallized from hot water. Elemental analysis conformed to the formula for compound 1, and a single-crystal x-ray diffraction study confirmed the structure as a linear, two-coordinate complex with gold-sulfur bond lengths averaging 2.27 angstroms.

Workup

  1. customDark orange and red precipitates
  2. customformed initially
  3. dissolutiondissolved
  4. temperatureAfter cooling a few hours
  5. filtrationwhite platelets of the product were filtered (84% yield)
  6. dissolutionThis intermediate gold(I) compound (0.228 g) was dissolved in 4 mL water
  7. additionadded to a room temperature solution of 1,4,5-trimethyl-1,2,4-triazolium-3-thiolate (0.126 g)
  8. customto form
  9. filtrationwas filtered
  10. customafter standing in the refrigerator a few hours

Sources & evidence

ORD record
ord-323da858ea474b35896a7d0b27fc0258
Source dataset
uspto-grants-1991_09
Patent number
US05049485

Reaction notes

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