Triethylamine → HCID 10729813, compound

HRID 1534098Notes

Reaction equation

HRID 1534098 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([NH:9][C:10]([NH:12][C:13]([CH2:16][CH3:17])([CH3:15])[CH3:14])=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][C:13]([CH2:16][CH3:17])([CH3:14])[CH3:15])[CH:5]=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 10868DicyclohexylcarbodiimideHCID 10779909HCID 10779909, compound

Product 1

HCID 10729813HCID 10729813, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3.0 g of N-(3,5-dichlorophenyl)-N'-t-pentylthiourea produced in Example A-2 in 25 ml of THF were added 2.44 g of DCC and 0.36 g of triethylamine. The mixture was relfuxed for 3 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'-t-pentylcarbodiimide as an oil. To a solution of this oil in 30 ml of THF were added 1.0 g of cyanamide and 0.1 ml of diisopropylethylamine. The mixture was refluxed for 40 hours and evaporated in vacuo. The residue was recrytallized from diisopropyl ether-ethyl acetate mixture to give 1.9 g of the title compound as colorless needles melting at 151.0°-153.0° C.

Workup

  1. customevaporated in vacuo
  2. extractionThe residue was extracted with petroleum ether
  3. customThe extract was evaporated in vacuo

Sources & evidence

ORD record
ord-9d2db3e8fb6b4c8986fb411a548f9fb9
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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