2-Bromo-1,1-dimethoxyethane → HCID 57428870, compound

HRID 507666Notes

Reaction equation

HRID 507666 reaction equation
[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14](=[S:16])[NH2:15])=[CH:5][N:4]=1.CO[CH:19](OC)[CH2:20]Br>C(O)C.Cl>[CH3:1][S:2][C:3]1[N:8]=[C:7]([C:9]2[S:10][CH:11]=[CH:12][CH:13]=2)[C:6]([C:14]2[S:16][CH:19]=[CH:20][N:15]=2)=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 816722-Bromo-1,1-dimethoxyethane2×HCID 57428869HCID 57428869, compound

Product 1

HCID 57428870HCID 57428870, compoundYield 55.1%

Reagents, catalysts & solvents 2

HCID 313Hydrochloric AcidCatalystHCID 702EthanolSolvent

Procedure

2-(Methylthio)-4-(thiophen-2-yl)pyrimidine-5-carbothioamide (0.3 g, 1.12 mmol) suspended in ethanol (2 mL) was treated with bromoacetaldehyde dimethylacetal (0.158 mL, 1.34 mmol). The reaction was stirred at reflux overnight. No product formtion was obverved by thin layer chromatography in 20% ethyl acetate/hexanes. Another equivalent of bromoacetaldehyde dimethylacetal was added to the reaction in addition to a few drops of concentrated hydrochloric acid and the reaction kept at reflux for another 3 h. The reaction was cooled down to room temperature and the volatiles removed in vacuo. A solution of saturated sodium bicarbonate was added to the residue, which was extracted with dichloromethane. The organic layer was dried with sodium sulfate and purified by flash chromatography using a gradient of 20 to 60% of ethyl acetate in hexanes. The product was obtained as a brown solid (0.18 g). MS (M+H)+ 292.

Workup

  1. temperatureat reflux overnight
  2. temperatureat reflux for another 3 h
  3. customthe volatiles removed in vacuo
  4. additionA solution of saturated sodium bicarbonate was added to the residue, which
  5. extractionwas extracted with dichloromethane
  6. dry with materialThe organic layer was dried with sodium sulfate
  7. custompurified by flash chromatography

Sources & evidence

ORD record
ord-6a088561cf1f4b4086cab8fd0220feb1
Source dataset
uspto-grants-2010_08
Patent number
US07786132B2

Reaction notes

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