Benzoyl chloride → HCID 178513058, compound

HRID 433340Notes

Reaction equation

HRID 433340 reaction equation
[C:1]([NH:4][NH:5][C:6](=[O:13])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1)(=[NH:3])[NH2:2].C(=O)([O-])[O-].[Na+].[Na+].[C:20](Cl)(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1>CN(C)C=O>[C:20]([NH:3][C:1]([NH:4][NH:5][C:6](=[O:13])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1)=[NH:2])(=[O:27])[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 7412Benzoyl chlorideHCID 10340Sodium CarbonateHCID 178513166HCID 178513166, compound

Product 1

HCID 178513058HCID 178513058, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
20 °C

Procedure

A four neck flask (one liter) equipped with a thermometer and a stirrer was charged with 71.3 g (0.4 mole) of N′-amidinobenzoic acid hydrazide (CAS. 3679-92-3), 46.6 g (0.44 mole) of anhydrous sodium carbonate and 360 cc of dimethylformamide. Dropwise added thereto in about 2 hours was 59.0 g (0.42 mole) of benzoyl chloride under stirring while cooling so that the temperature was maintained at 20° C. or lower. After stirring at 20° C. (room temperature) for 12 hours, deposited crystals were filtered off, and the mother liquor was concentrated under reduced pressure. The resulting residue was dissolved in 100 cc of isopropyl alcohol, and the solution was slowly dropwise added to one liter of deionized water to deposit crystals. The resulting crystals were filtered off, sufficiently washed with deionized water and then dried under reduced pressure, whereby the intended compound (pale yellow crystals) was obtained.

Workup

  1. customA four neck flask (one liter) equipped with a thermometer and a stirrer
  2. additionDropwise added
  3. temperaturewhile cooling so that the temperature
  4. filtrationwere filtered off
  5. concentrationthe mother liquor was concentrated under reduced pressure
  6. dissolutionThe resulting residue was dissolved in 100 cc of isopropyl alcohol
  7. additionthe solution was slowly dropwise added to one liter of deionized water
  8. filtrationThe resulting crystals were filtered off
  9. washsufficiently washed with deionized water
  10. customdried under reduced pressure, whereby the intended compound (pale yellow crystals)
  11. customwas obtained

Sources & evidence

ORD record
ord-37f04ba3d7e94dc28634ab51755fa119
Source dataset
uspto-grants-2003_12
Patent number
US06667356B2

Reaction notes

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