Water → HCID 23458904, compound

HRID 1680046Notes

Reaction equation

HRID 1680046 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([CH2:6][NH:7][C:8]2[CH:18]=[CH:17][C:11]([C:12]([O:14][CH2:15][CH3:16])=[O:13])=[CH:10][CH:9]=2)=[CH:4][CH:3]=1.Cl[C:22]([O:24][CH2:25][CH3:26])=[O:23].O>N1C=CC=CC=1>[CH2:15]([O:14][C:12]([C:11]1[CH:17]=[CH:18][C:8]([N:7]([CH2:6][C:5]2[CH:19]=[CH:20][C:2]([Cl:1])=[CH:3][CH:4]=2)[C:22](=[O:23])[O:24][CH2:25][CH3:26])=[CH:9][CH:10]=1)=[O:13])[CH3:16]

Participants

5

Reactant 3

HCID 962WaterHCID 10928Ethyl chloroformateHCID 773384Benzoic acid, 4-[[(4-chlorophenyl)methyl]amino]-, ethyl ester

Product 1

HCID 23458904HCID 23458904, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
100 °C

Procedure

A stirred solution of ethyl 4-(4-chlorobenzylamino)-benzoate (5.8 g; 0.02 mole) in pyridine (50 ml) was treated dropwise with ethyl chloroformate (2.5 g; 0.023 mole) at room temperature. The mixture was heated to 100° C. for 30 minutes, cooled and added to iced water (100 ml). After neutralisation with dilute hydrochloric acid the product was extracted into dichloromethane (2×100 ml), washed with water (1×100 ml), dried (anhydrous MgSO4) and the solvent evaporated. The residual oil was purified by chromatography on silica-gel in dichloromethane to give ethyl N-(4-ethoxycarbonylphenyl)-N-(4-chlorobenzyl)-carbamate as a colourless oil (4.86 g; 56%) which solidifed on standing. M.p. 43°-6° C.

Workup

  1. temperaturecooled
  2. extractionAfter neutralisation with dilute hydrochloric acid the product was extracted into dichloromethane (2×100 ml)
  3. washwashed with water (1×100 ml)
  4. dry with materialdried (anhydrous MgSO4)
  5. customthe solvent evaporated
  6. customThe residual oil was purified by chromatography on silica-gel in dichloromethane

Sources & evidence

ORD record
ord-8e7c6abb66d6406d9b83c5e56593b1b6
Source dataset
uspto-grants-1981_06
Patent number
US04271188

Reaction notes

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