Formic Acid → HCID 11378844, compound

HRID 967776Notes

Reaction equation

HRID 967776 reaction equation
Cl.C(N=C=NCCCN(C)C)C.[NH2:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18].[CH:24](O)=[O:25]>ClCCl>[CH:24]([NH:13][C:14]1[CH:15]=[C:16]([CH:21]=[CH:22][CH:23]=1)[C:17]([O:19][CH3:20])=[O:18])=[O:25]

Participants

5

Reactant 3

HCID 284Formic AcidHCID 78274Benzoic acid, 3-amino-, methyl esterHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 11378844HCID 11378844, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride (2.47 g) was added to a mixture of methyl 3-aminobenzoate (1.50 g), formic acid (748 μL) and dichloromethane (15 mL) under cooling with ice-water, and the mixture was stirred at the same temperature for ten minutes under nitrogen atmosphere and stirred at room temperature for fourteen hours. The reaction mixture was poured into ice-water (30 mL) to be separated and the aqueous layer was extracted with dichloromethane. The organic layer was washed with water and an aqueous sodium hydrogencarbonate solution successively, and dried over anhydrous sodium sulfate. After the solvent was removed under reduced pressure, the residue obtained was washed with ether and dried to obtain the titled compound (1.61 g) as crystals.

Workup

  1. stirringstirred at room temperature for fourteen hours
  2. customto be separated
  3. extractionthe aqueous layer was extracted with dichloromethane
  4. washThe organic layer was washed with water
  5. dry with materialan aqueous sodium hydrogencarbonate solution successively, and dried over anhydrous sodium sulfate
  6. customAfter the solvent was removed under reduced pressure
  7. customthe residue obtained
  8. washwas washed with ether
  9. customdried

Sources & evidence

ORD record
ord-2661eef80e43442682cd2a5f922a6994
Source dataset
uspto-grants-2005_10
Patent number
US06956046B2

Reaction notes

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