Phosgene → HCID 22614049, compound

HRID 842426Notes

Reaction equation

HRID 842426 reaction equation
Cl.[NH2:2][CH2:3][C:4]1[CH:19]=[CH:18][C:7]([C:8]([O:10][CH2:11][C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)=[O:9])=[CH:6][CH:5]=1.[C:20]([O-])(O)=[O:21].[Na+].C(Cl)(Cl)=O>ClCCl>[CH2:11]([O:10][C:8]([C:7]1[CH:6]=[CH:5][C:4]([CH2:3][N:2]=[C:20]=[O:21])=[CH:19][CH:18]=1)=[O:9])[C:12]1[CH:13]=[CH:14][CH:15]=[CH:16][CH:17]=1

Participants

5

Reactant 3

HCID 6371PhosgeneHCID 516892Sodium BicarbonateHCID 21978317HCID 21978317, compound

Product 1

HCID 22614049HCID 22614049, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To 4-(aminomethyl)benzoic acid, benzyl ester, hydrochloride salt, prepared as in Example 5, step C (288 mg, 1.04 mmol) at 0° C. was added saturated aqueous NaHCO3 (15 ml) and dichloromethane (20 ml). After 20 minutes stirring was ceased and the two layers were allowed to separate. Phosgene (20% solution in toluene, 1.1 ml, 2.18 mmol) was added rapidly to the lower layer and stirring resumed immediately. After 1 hour the organic layer was isolated. The aqueous layer was extracted with dichloromethane (3×20 ml). The four organic layers were combined, dried (Na2SO4) and concentrated in vacuo to give the title compound (261 mg, 94%) as an oil.

Workup

  1. customto separate
  2. stirringstirring
  3. customAfter 1 hour the organic layer was isolated
  4. extractionThe aqueous layer was extracted with dichloromethane (3×20 ml)
  5. dry with materialdried (Na2SO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-0e96fc566f8b44c7bc98bef69a698dec
Source dataset
uspto-grants-2002_04
Patent number
US06375926B1

Reaction notes

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