O-Toluidine → HCID 69709438, compound

HRID 430526Notes

Reaction equation

HRID 430526 reaction equation
N[C:2]1[C:3](C)=[CH:4]C=[CH:6][CH:7]=1.[C:9]([CH2:11][C:12]([OH:14])=[O:13])#[N:10].O[N:16]1C2C=CC=CC=2N=N1.Cl.CN(C)CCCN=C=NCC>CN(C)C1C=CN=CC=1.C(Cl)Cl>[C:3]1([CH3:4])[C:11]([C:12]([NH2:16])=[O:14])=[CH:9][CH:6]=[CH:7][CH:2]=1.[C:9]([CH2:11][C:12]([OH:14])=[O:13])#[N:10]

Participants

7

Reactant 4

HCID 7242O-ToluidineHCID 9740Cyanoacetic acidHCID 757711-HydroxybenzotriazoleHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochloride

Product 1

HCID 69709438HCID 69709438, compoundYield 57%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

A mixture of o-toluidine (5.0 mL, 47 mmol), methylene chloride (15 mL), cyanoacetic acid (8.0 g, 94 mmol), 1-hydroxybenzotriazole (12.7 g, 94 mmol), 4-dimethylaminopyridine (5 crystals, catalytic amount), and 1-(3dimethylaminopropyl)-3-ethylcarbodiimide hydrochloride (16.2 g, 94 mmol) was stirred at ambient temperature overnight. The reaction was concentrated and the residual pale yellow oil was partitioned between ethyl acetate and water. The phases were separated and the organic layer was washed with saturated sodium bicarbonate and brine, dried over sodium sulfate, and concentrated to 5.2 g of off-white solid. This solid was recrystallized from methylene chloride in two crops to afford cyanoacetic acid o-toluamide (4.71 g, 57%) as white crystals.

Workup

  1. concentrationThe reaction was concentrated
  2. customthe residual pale yellow oil was partitioned between ethyl acetate and water
  3. customThe phases were separated
  4. washthe organic layer was washed with saturated sodium bicarbonate and brine
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated to 5.2 g of off-white solid
  7. customThis solid was recrystallized from methylene chloride in two crops

Sources & evidence

ORD record
ord-8242ec3e2d654b60a44c9005c0c1fcb4
Source dataset
uspto-grants-2001_11
Patent number
US06323208B1

Reaction notes

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