2-Chlorobenzaldehyde → HCID 86652007, compound

HRID 1010541Notes

Reaction equation

HRID 1010541 reaction equation
ClC1N=CC(C[NH:9][CH2:10][CH2:11][N:12]2[CH2:16][CH2:15][NH:14][C:13]2=[CH:17][N+:18]([O-:20])=[O:19])=CC=1.[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH:24]=O.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].S([O-])([O-])(=O)=O.[Mg+2]>ClCCCl>[Cl:21][C:22]1[CH:29]=[CH:28][CH:27]=[CH:26][C:23]=1[CH2:24][NH:9][CH2:10][CH2:11][N:12]1[CH2:16][CH2:15][NH:14][C:13]1=[CH:17][N+:18]([O-:20])=[O:19]

Participants

6

Reactant 4

HCID 69962-ChlorobenzaldehydeHCID 24083Sulfuric acid magnesium salt (1:1)HCID 5049666Sodium triacetoxyborohydrideHCID 86652006HCID 86652006, compound

Product 1

HCID 86652007HCID 86652007, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

With stirring and cooling in an ice-water bath (0° C.) 0.12 grams (0.0004 mole) of [(6-chloro(3-pyridyl))methyl]{2-[2-(nitromethylene)imidazolidinyl]ethyl]amine, 0.06 gram (0.0004 mole) of 2-chlorobenzaldehyde, 0.13 gram (0.0006 mole) of sodium triacetoxyborohydride and 0.10 gram (0.0008 mole) of magnesium sulfate in about 20 mL of 1,2-dichloroethane were combined. Upon completion of addition, the cooling bath was removed and the reaction mixture was allowed to warm to ambient temperature as it stirred during an 18 hour period. After this time the reaction was quenched by the addition of five mL of water, then the reaction mixture was neutralized to pH of 8-9. The reaction mixture was then extracted with two 50 mL portions of methylene chloride. The combined extracts were dried with sodium sulfate, filtered and concentrated under reduced pressure, yielding 0.07 gram of Compound 501. The

Workup

  1. additionUpon completion of addition
  2. customthe cooling bath was removed
  3. stirringstirred during an 18 hour period
  4. customAfter this time the reaction was quenched by the addition of five mL of water
  5. extractionThe reaction mixture was then extracted with two 50 mL portions of methylene chloride
  6. dry with materialThe combined extracts were dried with sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef9794a0c4b7466ea036db344c5f5eaa
Source dataset
uspto-grants-2011_07
Patent number
US07977332B2

Reaction notes

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