Methyl chloroformate → Ethyl benzoate

HRID 2051605Notes

Reaction equation

HRID 2051605 reaction equation
C(OC1N=CC=CC=1C(O)=O)CCC.C(N(CC)CC)C.COC(Cl)=O.Cl.[CH2:28]([O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][C:35](CCN)=[CH:34][CH:33]=1)[CH3:29]>O1CCCC1>[CH2:28]([O:30][C:31](=[O:41])[C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[CH3:29]

Participants

6

Reactant 4

HCID 6586Methyl chloroformateHCID 8471TriethylamineHCID 12945885Ethyl 4-(2-aminoethyl)benzoate--hydrogen chloride (1/1)HCID 22667896HCID 22667896, compound

Product 1

HCID 7165Ethyl benzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

6.5 g of 2-butoxy-nicotinic acid (melting point= m.p. 54°-56° C., from acetic acid ethyl ester) are dissolved in 150 ml of tetrahydrofuran. After addition of 14.5 ml of triethylamine, the batch is cooled to 0° C., and 3.2 ml of chloroformic acid methyl ester are added dropwise. Agitation is continued for one hour at 0° C., 7.6 g of 4-(2-aminoethyl)-benzoic acid ethyl ester-hydrochloride are added, agitation is continued for a further hour at 0° C., and subsequently for 4 hours at room temperature. The batch is evaporated and the residue is combined with acetic acid ethyl ester. After washing with water, sodium bicarbonate solution, dilute hydrochloric acid and water, the acetic acid ethyl ester solution is dried and evaporated under reduced pressure. The 4-(2-<2-butoxy-nicotin-amido>-ethyl)-benzoic acid ethyl ester so obtained is refluxed for 3 hours in 25 ml of 2 N sodium hydroxide solution and 50 ml of ethanol. After having distilled off the solvent, the product is dissolved in water and acidified with dilute acetic acid, suction-filtered and recrystallized from acetic ester. The 4-(2-<2-butoxy-nicotin-amido>-ethyl)-benzoic acid has a melting point of 147°-149° C.

Workup

  1. waitagitation is continued for a further hour at 0° C.
  2. waitsubsequently for 4 hours at room temperature
  3. customThe batch is evaporated
  4. washAfter washing with water, sodium bicarbonate solution, dilute hydrochloric acid and water
  5. dry with materialthe acetic acid ethyl ester solution is dried
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-2504d2fb3d5c4c4a9c340b53b29996c4
Source dataset
uspto-grants-1980_01
Patent number
US04181658

Reaction notes

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