Triethylamine → HCID 20244240, compound

HRID 1632579Notes

Reaction equation

HRID 1632579 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([CH:7]=[C:8]([C:10]([CH3:18])([CH3:17])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=1)[NH2:6].Br[CH:20]([CH2:25][CH2:26][CH2:27]Br)[CH2:21][C:22]([O-:24])=[O:23].C(N(CC)CC)C>C(OCC)C>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:6]2[CH2:27][CH2:26][CH2:25][CH:20]2[CH2:21][C:22]([OH:24])=[O:23])[CH:7]=[C:8]([C:10]([CH3:17])([CH3:18])[CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH3:16])[CH:9]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 20244258HCID 20244258, compoundHCID 86739684HCID 86739684, compound

Product 1

HCID 20244240HCID 20244240, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 24.9 g. (0.10 mole) 3-methoxy-5-(1,1-dimethylheptyl)aniline, 34.5 g. (0.12 mole) methyl dl-3,6-dibromocaproate, 15 g. triethylamine and 100 ml. ethyl ether is stirred under nitrogen at room temperature for 20 hours. The ether is evaporated and the residue heated at 90°-120° C. for three hours. Additional methyl dl-3,6-dibromocaproate (5 g.) and triethylamine (5 g.) is added and heating continued at 90° C. for 2 hours and finally at 120° C. for one hour. The reaction mixture is worked up as described in Example 16 to provide the methyl ester of the desired product which is hydrolyzed in methanolic sodium hydroxide by the method of Example 17 to provide the title acid.

Workup

  1. additionA mixture of 24.9 g
  2. customThe ether is evaporated
  3. temperaturethe residue heated at 90°-120° C. for three hours
  4. additionis added
  5. temperatureheating

Sources & evidence

ORD record
ord-8e43205887064f3588d3aac42b6f0819
Source dataset
uspto-grants-1984_10
Patent number
US04476131

Reaction notes

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