2,4-Diaminotoluene → HCID 20236238, compound

HRID 1277736Notes

Reaction equation

HRID 1277736 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[C:10](=[O:21])([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])N.[CH3:22][O-:23].[Na+]>C(O)CCCCCCC>[CH2:13]([O:12][C:10]([NH:1][C:2]1[CH:7]=[C:6]([NH:8][C:22]([O:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20])=[O:23])[CH:5]=[CH:4][C:3]=1[CH3:9])=[O:21])[CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH3:20]

Participants

5

Reactant 3

HCID 72612,4-DiaminotolueneHCID 16240Carbamic acid, octyl esterHCID 10942334Sodium Methoxide

Product 1

HCID 20236238HCID 20236238, compoundYield 81.7%

Reagents, catalysts & solvents 1

HCID 9571-OctanolSolvent

Procedure

In a reaction vessel, 61 parts of 2,4-diaminotoluene with 432 parts of octyl carbamate and 1.5 parts of sodium methanolate in 1950 parts of octanol are heated to the boiling point (195° C.). After 23 hours, the mixture is allowed to cool and excess octanol and excess octyl carbamate is removed by distillation to a sump temperature of 180° C. Using high pressure liquid chromatography, the residue is analyzed using the external standard method. It is determined that 57 percent of the 2,4-diaminotoluene reacted, resulting in 101 parts (81.7 percent of theory) of 2,4-bis(octoxycarbonylamino)toluene, C25H42O4N2 (molecular weight 434) and 10.9 parts (13.8 percent of theory) of a mixture consisting of 2-amino-4-(octoxycarbonylamino)toluene and 4-amino-2-(octoxycarbonylamino)toluene.

Workup

  1. temperatureto cool
  2. customexcess octanol and excess octyl carbamate is removed by distillation to a sump temperature of 180° C
  3. customreacted

Sources & evidence

ORD record
ord-5480b5fb65584b11b8953f9a5dce0352
Source dataset
uspto-grants-1981_07
Patent number
US04278805

Reaction notes

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