Hydrochloric Acid → HCID 57611946, compound

HRID 1919878Notes

Reaction equation

HRID 1919878 reaction equation
C1(C(=[N:14][CH:15]([C:21]2[CH:33]=[CH:32][C:24]([C:25]([O:27]C(C)(C)C)=[O:26])=[CH:23][CH:22]=2)[C:16]([O:18][CH2:19][CH3:20])=[O:17])C2C=CC=CC=2)C=CC=CC=1.Cl>C(OCC)C>[NH2:14][CH:15]([C:21]1[CH:33]=[CH:32][C:24]([C:25]([OH:27])=[O:26])=[CH:23][CH:22]=1)[C:16]([O:18][CH2:19][CH3:20])=[O:17]

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 57611901HCID 57611901, compound

Product 1

HCID 57611946HCID 57611946, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

Tert-butyl 4-{1-[(diphenylmethylene)amino]-2-ethoxy-2-oxoethyl}benzoate (17.4 g, 39.2 mmol) and 2N HCl (200 mL, 400 mmol) were stirred in diethyl ether (200 mL) at room temperature overnight. The aqueous phase was separated and concentrated in vacuo. The HCl salt was dissolved in water and 35 mL of 2N NaOH was added. The volume was reduced in vacuo and the resulting precipitate collected by filtration to give to give the desired product as a white solid. 1H NMR (DMSO-d6, 600 MHz) δ 7.88 (d, J=8.1 Hz, 2H), 7.47 (d, J=8.1 Hz, 2H), 4.60 (s, 1H), 4.04 (m, 2H), 1.09 (t, J=7.2 Hz, 3H). MS: cal'd 224 (MH+), exp 224 (MH+).

Workup

  1. customThe aqueous phase was separated
  2. concentrationconcentrated in vacuo
  3. dissolutionThe HCl salt was dissolved in water
  4. addition35 mL of 2N NaOH was added
  5. filtrationthe resulting precipitate collected by filtration
  6. customto give

Sources & evidence

ORD record
ord-0eab4be1cbf54a14881bb3760e0cb960
Source dataset
uspto-grants-2012_05
Patent number
US08168658B2

Reaction notes

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