Formaldehyde → HCID 19082696, compound

HRID 963768Notes

Reaction equation

HRID 963768 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][CH:9]=[CH:8][C:5]=1[CH2:6][Cl:7])([O-:3])=[O:2].[CH2:12]=[O:13].C1CCN2C(=NCCC2)CC1>CS(C)=O.CC(O)=O.C(Cl)Cl>[Cl:7][CH:6]([C:5]1[CH:8]=[CH:9][CH:10]=[CH:11][C:4]=1[N+:1]([O-:3])=[O:2])[CH2:12][OH:13]

Participants

7

Reactant 3

HCID 712FormaldehydeHCID 119212-Nitrobenzyl chlorideHCID 811841,8-Diazabicyclo(5.4.0)undec-7-ene

Product 1

HCID 19082696HCID 19082696, compound

Reagents, catalysts & solvents 3

HCID 176Acetic AcidCatalystHCID 679Dimethyl SulfoxideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of 2-nitrobenzyl chloride (4.3 g, 25 mmol) in DMSO (3.5 ml, synthesis quality, additionally dried for 2 d over molecular sieve 4 Å) was mixed with paraformaldehyde (750 mg, 25 mmol) and DBU (0.5 ml, 3.3 mmol) and stirred at room temperature for 20 min. The pH value of the reaction mixture was adjusted to about pH 3 by means of a few drops of conc. AcOH. The mixture was diluted with CH2Cl2 (120 ml), washed with H2O (80 ml) and post-extracted with CH2Cl2 (2×100 ml).

Workup

  1. customadditionally dried for 2 d over molecular sieve 4 Å)
  2. washwashed with H2O (80 ml)
  3. extractionpost-extracted with CH2Cl2 (2×100 ml)

Sources & evidence

ORD record
ord-f58d6b66d59d421a977cea714a5deb8a
Source dataset
uspto-grants-1998_06
Patent number
US05763599

Reaction notes

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