Formaldehyde → HCID 22479194, compound

HRID 1392171Notes

Reaction equation

HRID 1392171 reaction equation
[Br:1][C:2]1[CH:27]=[CH:26][C:5]([CH2:6][C:7]23[C:15](=[O:16])[N:14]([C:17]4[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=4)[C:13](=[O:25])[N:12]2[CH2:11][CH2:10][NH:9][CH2:8]3)=[CH:4][CH:3]=1.[CH2:28]=O>C(O)=O.O.CCOC(C)=O>[CH3:28][N:9]1[CH2:8][C:7]2([CH2:6][C:5]3[CH:26]=[CH:27][C:2]([Br:1])=[CH:3][CH:4]=3)[N:12]([C:13](=[O:25])[N:14]([C:17]3[CH:22]=[C:21]([Cl:23])[CH:20]=[C:19]([Cl:24])[CH:18]=3)[C:15]2=[O:16])[CH2:11][CH2:10]1

Participants

6

Reactant 2

HCID 712FormaldehydeHCID 22479108HCID 22479108, compound

Product 1

HCID 22479194HCID 22479194, compound

Reagents, catalysts & solvents 3

HCID 284Formic AcidSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 6-(4-bromobenzyl)-8-(3,5-dichlorophenyl)-1,4,8-triazabicyclo[4.3.0]nonane-7,9-dione (0.072 g) in formic acid (0.40 mL) and water (0.10 mL) was added 37% formaldehyde (0.050 mL). After 1 hour at reflux, the reaction mixture was diluted with EtOAc and the solution washed with aqueous NaHCO3, and brine, dried (Na2SO4), filtered, and concentrated to yield the titled compound (74.3 g). MS (m/z) 482 (MH+). mp 221° C.

Workup

  1. temperatureAfter 1 hour at reflux
  2. washthe solution washed with aqueous NaHCO3, and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-70bab9060e224afda5bbf915d8e43b28
Source dataset
uspto-grants-2008_03
Patent number
US07342012B2

Reaction notes

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