Formic Acid → HCID 18928235, compound

HRID 1599387Notes

Reaction equation

HRID 1599387 reaction equation
[Cl:1][C:2]1[CH2:8][CH:7]2[NH:9][CH:4]([CH2:5][CH2:6]2)[C:3]=1[C:10]1[C:11]([Cl:15])=[N:12][S:13][N:14]=1.C=O.[CH:18](O)=O.C(=O)([O-])[O-].[K+].[K+]>O>[CH3:18][N:9]1[CH:7]2[CH2:6][CH2:5][CH:4]1[C:3]([C:10]1[C:11]([Cl:15])=[N:12][S:13][N:14]=1)=[C:2]([Cl:1])[CH2:8]2

Participants

6

Reactant 4

HCID 284Formic AcidHCID 712FormaldehydeHCID 11430Potassium CarbonateHCID 21708644HCID 21708644, compound

Product 1

HCID 18928235HCID 18928235, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 3-chloro-2-(3-chloro-1,2,5-thiadiazol-4-yl)-8-azabicyclo[3.2.1]oct-2-ene (1.0 g, 3.8 mmol), formaldehyde (37% water solution, 10 ml) and formic acid (6.0 ml) was heated at reflux for 2 h. After cooling water was added (100 ml) and the water solution was made basic with potassium carbonate. The water solution was extracted with diethylether (3×50 ml). The organic extracts were dried over magnesium sulfate and evaporated. The residue was crystallized as the oxalate salt from acetone in 1.2 g yield.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 2 h
  3. additionwas added (100 ml)
  4. extractionThe water solution was extracted with diethylether (3×50 ml)
  5. dry with materialThe organic extracts were dried over magnesium sulfate
  6. customevaporated
  7. customThe residue was crystallized as the oxalate salt from acetone in 1.2 g
  8. customyield

Sources & evidence

ORD record
ord-88dc4eddccba410283a90b1aec302e14
Source dataset
uspto-grants-1998_04
Patent number
US05741788

Reaction notes

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