Carbon Dioxide → HCID 68242896, compound

HRID 1624218Notes

Reaction equation

HRID 1624218 reaction equation
[CH3:1][C:2]1[S:3][C:4]2[C:5](=[CH:7][S:8][CH:9]=2)[N:6]=1.C(=O)=O.[Br:13]N1C(=O)CCC1=O.[Cl-].[Na+]>O1CCCC1>[Br:13][C:9]1[S:8][CH:7]=[C:5]2[C:4]=1[S:3][C:2]([CH3:1])=[N:6]2

Participants

6

Reactant 4

HCID 280Carbon DioxideHCID 5234Sodium ChlorideHCID 67184N-bromobutanimideHCID 9812833HCID 9812833, compound

Product 1

HCID 68242896HCID 68242896, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

1 mmol of 2-methylthieno[3,4-d][1,3]thiazole represented by formula (12) was dissolved in 10 ml of tetrahydrofuran and kept at −78° C. in a methanol-bath cooled by dry ice. Into this solution, a solution comprised of 1.05 mmol of N-bromosuccinimide and 5 ml of tetrahydrofran was gradually added dropwise. After two hours reaction, an excess amount of a saturated sodium chloride aqueous solution was added to stop the reaction. The reacted liquid was washed with water, and the organic layer was recovered and dried under sodium sulfate. The solvent was evaporated out and then purification was carried out using column separation method with solvents of ethylacetate and hexane, obtaining 6-bromo-2-methylthieno[3,4-d][1,3]thiazole represented by formula (13).

Workup

  1. customkept at −78° C. in a methanol-bath
  2. additionwas gradually added dropwise
  3. customAfter two hours reaction
  4. customthe reaction
  5. washThe reacted liquid was washed with water
  6. customthe organic layer was recovered
  7. customdried under sodium sulfate
  8. customThe solvent was evaporated out
  9. custompurification
  10. customcolumn separation method with solvents of ethylacetate and hexane

Sources & evidence

ORD record
ord-de8804209b204731a4d472f89cdfd702
Source dataset
uspto-grants-2014_07
Patent number
US08779086B2

Reaction notes

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