Ethyl 4-bromobutyrate → HCID 20202782, compound

HRID 978370Notes

Reaction equation

HRID 978370 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-1fc9ced34647468eaebdb89923200b17
Source dataset
uspto-grants-1987_05
Patent number
US04665073

Reaction notes

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