Formaldehyde → HCID 56600137, compound

HRID 517772Notes

Reaction equation

HRID 517772 reaction equation
[CH2:1]=O.[NH:3]1[CH2:8][CH2:7][O:6][CH2:5][CH2:4]1.C[Si]([N:13]=[N+:14]=[N-:15])(C)C.[N+:16]([C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)#[C-:17]>CO>[F:26][C:24]([F:27])([F:25])[C:21]1[CH:22]=[CH:23][C:18]([N:16]2[C:17]([CH2:1][N:3]3[CH2:8][CH2:7][O:6][CH2:5][CH2:4]3)=[N:15][N:14]=[N:13]2)=[N:19][CH:20]=1

Participants

6

Reactant 4

HCID 712FormaldehydeHCID 8083MorpholineHCID 78378AzidotrimethylsilaneHCID 552654302-Isocyano-5-(trifluoromethyl)pyridine

Product 1

HCID 56600137HCID 56600137, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of formaldehyde (37% in water) (0.043 ml, 0.581 mmol) in methanol (2 ml) was added morpholine (0.051 ml, 0.581 mmol). The reaction mixture was stirred at room temperature for 2 hours before the addition of trimethylsilylazide (0.077 ml, 0.581 mmol) and 2-isocyano-5-(trifluoromethyl)pyridine (100 mg, 0.581 mmol, commercially available from Priaxon AG, Munich, Germany). The reaction mixture was stirred at room temperature for 18 hours. The reaction mixture was partitioned between DCM (50 ml) and water (20 ml). The aqueous layer was extracted with DCM (50 ml). The organic layers were combined and passed through a phase separator, then concentrated. The residue was purified by MDAP. Relevant fractions were combined to afford the title compound as a light yellow solid (7 mg).

Workup

  1. customThe reaction mixture was partitioned between DCM (50 ml) and water (20 ml)
  2. extractionThe aqueous layer was extracted with DCM (50 ml)
  3. concentrationconcentrated
  4. customThe residue was purified by MDAP

Sources & evidence

ORD record
ord-5dac2ab2149a4b1b879a4011223a7db2
Source dataset
uspto-grants-2015_08
Patent number
US09115132B2

Reaction notes

Loading…