Triethylamine → Ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate

HRID 484576Notes

Reaction equation

HRID 484576 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].C(N(CC)CC)C.[CH2:20]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42](Cl)=[O:43])=[CH:37][CH:36]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]>C(Cl)Cl>[CH2:20]([O:34][C:35]1[CH:40]=[CH:39][C:38]([CH2:41][C:42]([NH:1][C:2]2[CH:3]=[C:4]([CH:10]=[CH:11][CH:12]=2)[C:5]([O:7][CH2:8][CH3:9])=[O:6])=[O:43])=[CH:37][CH:36]=1)[CH2:21][CH2:22][CH2:23][CH2:24][CH2:25][CH2:26][CH2:27][CH2:28][CH2:29][CH2:30][CH2:31][CH2:32][CH3:33]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 11400Ethyl 3-aminobenzoateHCID 10021844p-Tetradecyloxyphenylacetylchloride

Product 1

HCID 15030160Ethyl 3-[[[4-(tetradecyloxy)phenyl]acetyl]amino]benzoate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 10.13 g of ethyl 3-amino-benzoate and 6.82 g of triethylamine in 100 ml of methylene chloride is added dropwise to a solution of p-tetradecyloxyphenylacetyl chloride in 100 ml of methylene chloride over 15 minutes. The mixture is stirred for an additional 2.5 hours then washed with dilute hydrochloric acid. The organic layer is evaporated and the residue dissolved in 1.5 liter of ether then washed with dilute sodium hydroxide. The organic layer is dried and evaporated to a residue which is crystallized from carbon tetrachloride:hexane to give 24.4 g of the desired product as a white solid, m.p. 91°-94° C.

Workup

  1. washthen washed with dilute hydrochloric acid
  2. customThe organic layer is evaporated
  3. dissolutionthe residue dissolved in 1.5 liter of ether
  4. washthen washed with dilute sodium hydroxide
  5. customThe organic layer is dried
  6. customevaporated to a residue which
  7. customis crystallized from carbon tetrachloride

Sources & evidence

ORD record
ord-3bcd2f06f67241a0a73e68a0710ad734
Source dataset
uspto-grants-1993_07
Patent number
US05231182

Reaction notes

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