Ethanol → 30714-89-7

HRID 2166660Notes

Reaction equation

HRID 2166660 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[CH3:9].[CH2:10]([O:12][C:13](=[O:15])N)[CH3:11].[CH:16]1([OH:22])[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]1.[CH2:23]([OH:25])C>[Cl-].[Tl+]>[CH:10]1([O:12][C:13]([NH:1][C:2]2[CH:7]=[C:6]([NH:8][C:23]([O:22][CH:16]3[CH2:21][CH2:20][CH2:19][CH2:18][CH2:17]3)=[O:25])[CH:5]=[CH:4][C:3]=2[CH3:9])=[O:15])[CH2:4][CH2:3][CH2:2][CH2:7][CH2:11]1

Participants

6

Reactant 4

HCID 702EthanolHCID 5641Carbamic acid, ethyl esterHCID 72612,4-DiaminotolueneHCID 7966Cyclohexanol

Product 1

HCID 441004430714-89-7

Reagents, catalysts & solvents 1

HCID 167263Thallium chlorideCatalyst

Conditions

Temperature
200 °C

Procedure

##STR3## (0.125 mol), 61 g of 2,4-diamino-toluene (0.5 mol), 100 g carbamic acid ethyl ester (1.125 mols), 200 g cyclohexanol (2 mols) and 3 g thallium chloride were heated to 140° C. The ethyl alcohol formed was distilled off and the reaction temperature was raised to 200° C. and maintained at that temperature for 7 hours. Any cyclohexanol remaining in the mixture was distilled off under a water jet vacuum and the residue was subsequently mixed with a little acetic ester. The reaction mixture crystallized completely overnight. 284 g of 2,4-bis-(cyclohexoxy carbonylamino)-toluene (76% of the theoretical yield) having a melting point of 156° C. (from toluene) were produced.

Workup

  1. distillationwas distilled off
  2. temperaturemaintained at that temperature for 7 hours
  3. distillationAny cyclohexanol remaining in the mixture was distilled off under a water jet vacuum
  4. additionthe residue was subsequently mixed with a little acetic ester
  5. customThe reaction mixture crystallized completely overnight

Sources & evidence

ORD record
ord-a8034ef0a0d8492d9e12eb891c175861
Source dataset
uspto-grants-1983_06
Patent number
US04388238

Reaction notes

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