Carbon Tetrachloride → N,N'-Methanetetraylbis(benzenamine)

HRID 2118665Notes

Reaction equation

HRID 2118665 reaction equation
[C:1]1([NH:7][C:8]([NH:10][C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=S)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(Cl)(Cl)(Cl)Cl>C(Cl)Cl>[C:11]1([N:10]=[C:8]=[N:7][C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:12]=[CH:13][CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 5943Carbon TetrachlorideHCID 11776TriphenylphosphineHCID 700999Diphenylthiourea

Product 1

HCID 98693N,N'-Methanetetraylbis(benzenamine)

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1,3-Diphenylthiourea (22.8 g), triphenylphosphine (10.1 g) triethylamine (10.1 g) and carbon tetrachloride (21.6 g) were refluxed for 4 hours in methylene chloride (300 ml). The solvent was removed under vacuum. The residue was shaken with hexane (300 ml); the hexane solution was evaporated and the residue was distilled to afford the title compound as an oil bp 115°-120°/0.3 mm. Similarly, by using this procedure, but employing other 1,3-disubstituted thioureas instead of 1,3-diphenylthiourea, other carbodiimides can be made.

Workup

  1. customThe solvent was removed under vacuum
  2. customthe hexane solution was evaporated
  3. distillationthe residue was distilled

Sources & evidence

ORD record
ord-54bcd869bf05439eadbfa7ae004636c1
Source dataset
uspto-grants-1987_07
Patent number
US04680300

Reaction notes

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