Cyanamide → HCID 178449178, compound

HRID 1534104Notes

Reaction equation

HRID 1534104 reaction equation
[C:1]([NH:5][C:6]([NH:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)=S)([CH3:4])([CH3:3])[CH3:2].[N:17]#[C:18][NH2:19].C1CCC(N=C=NC2CCCCC2)CC1.C(N(C(C)C)CC)(C)C>C1COCC1>[C:1]([NH:5][C:6]([NH:19][C:18]#[N:17])=[N:8][C:9]1[CH:14]=[C:13]([F:15])[CH:12]=[C:11]([F:16])[CH:10]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 4

HCID 9864CyanamideHCID 10868DicyclohexylcarbodiimideHCID 81531DiisopropylethylamineHCID 15020150HCID 15020150, compound

Product 1

HCID 178449178HCID 178449178, compoundYield 32.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1.5 g of N-t-butyl-N'-(3,5-difluorophenyl)thiourea produced in Example A-8 in 27 ml of THF were added 0.46 g of cyanamide, 2.2 g of DCC and 0.14 ml of diisopropylethylamine. The mixture was refluxed for 24 hours and evaporated in vacuo. The residue was mixed with 100 ml of benzene and the resulting crystals were filtered off. The filtrate was concentrated in vacuo. The residue was purified by silica gel column chromatography using a 9:1 mixture of benzene-ethyl acetate as a solvent to give 0.8 g of crude product. Recrystallization from benzene-cyclohexane mixture gave 0.5 g of the title compound as colorless needles melting at 170.0°-172.0° C.

Workup

  1. temperatureThe mixture was refluxed for 24 hours
  2. customevaporated in vacuo
  3. additionThe residue was mixed with 100 ml of benzene
  4. filtrationthe resulting crystals were filtered off
  5. concentrationThe filtrate was concentrated in vacuo
  6. customThe residue was purified by silica gel column chromatography
  7. additiona 9:1 mixture of benzene-ethyl acetate as a solvent
  8. customto give 0.8 g of crude product
  9. customRecrystallization from benzene-cyclohexane mixture

Sources & evidence

ORD record
ord-5453fbc456ef4c8299466cc171ad2813
Source dataset
uspto-grants-1992_02
Patent number
US05087640

Reaction notes

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