2,4-Diaminotoluene → HCID 6481333, compound

HRID 1857598Notes

Reaction equation

HRID 1857598 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]=[C:9]=[S:10])=[CH:4][CH:3]=1.[NH2:11][C:12]1[CH:17]=[C:16]([NH2:18])[CH:15]=[CH:14][C:13]=1[CH3:19]>O1CCOCC1>[CH3:19][C:13]1[CH:14]=[CH:15][C:16]([NH:18][C:9]([NH:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[S:10])=[CH:17][C:12]=1[NH:11][C:9]([NH:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1)=[S:10]

Participants

4

Reactant 2

HCID 72612,4-DiaminotolueneHCID 164804-Chlorophenyl isothiocyanate

Product 1

HCID 6481333HCID 6481333, compound

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent2×

Procedure

A solution of 4-chlorophenylisothiocyanate (1.39 g, 8.20 mmol) in dry dioxane (20 mL) is added dropwise, under nitrogen atmosphere, to a solution of 2,4-diaminotoluene (0.5 g, 4.10 mmol) in dry dioxane (20 mL). After 72 hours of stirring at room temperature the mixture is heated to 80° C. for 6 hours, and the solvent is eliminated under reduced pressure. The oily residue obtained is stirred with IsprOH (25 mL) for 4 hours. The white solid that precipitates is filtered and washed with n-hexane (3×25 mL) and ethyl ether (3×25 mL). The title compound is obtained as white powder. mp: 93-95° C.

Workup

  1. temperatureis heated to 80° C. for 6 hours
  2. customThe oily residue obtained
  3. stirringis stirred with IsprOH (25 mL) for 4 hours
  4. customThe white solid that precipitates
  5. filtrationis filtered
  6. washwashed with n-hexane (3×25 mL) and ethyl ether (3×25 mL)

Sources & evidence

ORD record
ord-74b62b975ca34333afa5694be7056ee8
Source dataset
uspto-grants-2000_11
Patent number
US06147116

Reaction notes

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