Triethylamine → HCID 10516251, compound

HRID 1534102Notes

Reaction equation

HRID 1534102 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][CH:13]([CH3:18])[C:14]([CH3:17])([CH3:16])[CH3:15])=S)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C1CCC(N=C=NC2CCCCC2)CC1.C(N(CC)CC)C>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]([N:9]=[C:10]=[N:12][CH:13]([CH3:18])[C:14]([CH3:17])([CH3:16])[CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 3611989HCID 3611989, compound

Product 1

HCID 10516251HCID 10516251, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2.5 g of N-(3,5-dichlorophenyl)-N'-(1,2,2-trimethylpropyl)thiourea produced in Example A-6 in 50 ml of THF were added 2.2 g of DCC and 0.36 g of triethylamine. The mixture was refluxed for 4 hours and evaporated in vacuo. The residue was extracted with petroleum ether. The extract was evaporated in vacuo to give N-(3,5-dichlorophenyl)-N'-(1,2,2-trimethylpropyl)carbodiimide as an oil. To a solution of this oil in 20 ml of THF were added 1.0 g of cyanamide and 1 ml of diisopropylethylamine. The mixture was refluxed for 40 hours and evaporated in vacuo. The residue was recrystallized from benzene to give 1.2 g of the title compound as colorless needles melting at 154.0°-156.0° C.

Workup

  1. temperatureThe mixture was refluxed for 4 hours
  2. customevaporated in vacuo
  3. extractionThe residue was extracted with petroleum ether
  4. customThe extract was evaporated in vacuo

Sources & evidence

ORD record
ord-8dccf61f68c54a78b58886b8bb35c717
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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