Hydrochloric Acid → HCID 18705582, compound

HRID 363400Notes

Reaction equation

HRID 363400 reaction equation
[CH2:1]([O:3][C:4](=[O:38])[CH:5]([N:24]=C(C1C=CC=CC=1)C1C=CC=CC=1)[CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[CH3:2].C(O)C.[ClH:42]>C1COCC1>[ClH:42].[NH2:24][CH:5]([CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH2:22][CH3:23])[C:4]([O:3][CH2:1][CH3:2])=[O:38]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 702EthanolHCID 18705578HCID 18705578, compound

Product 1

HCID 18705582HCID 18705582, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of ethyl-N-(diphenylmethylene)-2-aminoeicosanoate prepared as in Example 28A (104 g, 0.200 mol) in a 1:1 mixture (300 ml) of absolute ethanol and THF was added 0.5N hydrochloric acid (1.0 l) at room temperature over 10 min. The resulting solution was stirred for 30 min. Ethanol and THF were removed in vacuo and the aqueous slurry was extracted with CH2Cl2 (4×1 l). The extracts were combined and dried (MgSO4). The solvent was removed in vacuo and the crude product was recrystallized from hexane to give 74.3 g (95% yield) of colorless needles: mp 91°-4° C.; 1H NMR (CDCl3) δ 0.88 (t, J=6.6 Hz, 3 H), 1.26 (m, 33 H), 1.43 (m, 1 H), 1.56 (m, 1 H), 2.03 (quart, J=7.4 Hz, 2 H), 4.03 (m, 1 H), 4.27 (m, 2 H), 8.84 (br s, 3 H).

Workup

  1. customEthanol and THF were removed in vacuo
  2. extractionthe aqueous slurry was extracted with CH2Cl2 (4×1 l)
  3. dry with materialdried (MgSO4)
  4. customThe solvent was removed in vacuo
  5. customthe crude product was recrystallized from hexane

Sources & evidence

ORD record
ord-b91a657a706e4cf28ace82c26329f249
Source dataset
uspto-grants-1999_02
Patent number
US05874421

Reaction notes

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