Ethyl 4-bromobutyrate → HCID 20202782, compound

HRID 543751Notes

Reaction equation

HRID 543751 reaction equation
[NH:1]1[CH:8]=[CH:7][C:5]([NH2:6])=[N:4][C:2]1=[S:3].Br[CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14].N12CCCCC1C=NCCC2.[F:29][C:30]([F:36])([F:35])[CH2:31][N:32]=[C:33]=[S:34].[N-]=C=S>C(#N)C>[F:29][C:30]([F:36])([F:35])[CH2:31][NH:32][C:33](=[S:34])[NH:6][C:5]1[CH:7]=[CH:8][N:1]=[C:2]([S:3][CH2:10][CH2:11][CH2:12][C:13]([O:15][CH2:16][CH3:17])=[O:14])[N:4]=1

Participants

7

Reactant 5

HCID 76300Ethyl 4-bromobutyrateHCID 3141121,5-Diazabicyclo(5,4,0)undec-5-eneHCID 138837771,1,1-Trifluoro-2-isothiocyanatoethaneHCID 178418790HCID 178418790, compoundHCID 178507915HCID 178507915, compound

Product 1

HCID 20202782HCID 20202782, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-thiocytosine (0.64 g.), ethyl 4-bromobutyrate (1.07 g.) and 1,5-diazabicyclo[5,4,0]undec-5-ene (0.84 g.) was stirred for 4 hours and then evaporated to dryness. The residue was treated with water and the mixture extracted with EtOAc, and the extract dried and evaporated to dryness to give a gum (1.9 g.). The gum was dissolved in acetonitrile (5 ml.) the solution treated with 2,2,2-trifluoroethyl isothiocyanate (1.1 g.) and the mixture heated at 70° for 72 hours with the addition of further portions of isothiocyanate (0.5 g.) at 24 and 48 hours. The mixture was cooled and the solid which crystallised was collected to give ethyl 4-[4-(3-[2,2,2-trifluoroethyl]thioureido)pyrimid-2-ylthio]butyrate, m.p. 104°-106°.

Workup

  1. customevaporated to dryness
  2. additionThe residue was treated with water
  3. extractionthe mixture extracted with EtOAc
  4. customthe extract dried
  5. customevaporated to dryness
  6. customto give a gum (1.9 g.)
  7. temperatureThe mixture was cooled
  8. customthe solid which crystallised
  9. customwas collected

Sources & evidence

ORD record
ord-a37333cbc37c40af9ae9847ce3058d74
Source dataset
uspto-grants-1984_05
Patent number
US04447441

Reaction notes

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