Triethylamine → HCID 15583177, compound

HRID 2418208Notes

Reaction equation

HRID 2418208 reaction equation
[C:1]([O:10][CH3:11])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[NH2:4].C(N(CC)CC)C.[CH2:19]([N:22]=[C:23]=[O:24])[CH2:20][CH3:21]>C(Cl)Cl>[CH2:19]([NH:22][C:23]([NH:4][C:3]1[C:2](=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:1]([O:10][CH3:11])=[O:9])=[O:24])[CH2:20][CH3:21]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 61033Propyl isocyanate

Product 1

HCID 15583177HCID 15583177, compoundYield 95%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of 159 g of methyl anthranilate (1.053 mole), 5 ml of triethylamine and 134 g of n-propylisocyanate (1.58 mole) in 700 ml of petroleum ether (60°-80° C.) was refluxed for seventeen hours until TLC (CH2Cl2, silica) indicated that no methyl antranilate remained. The mixture was cooled and the precipitate was filtered off, washed with a little cold petroleum ether and dried under vacuum at room temperature to obtain 236 g (95% yield) of methyl N-(N'-n-propylcarbamoyl)-anthranilate melting at 101.5°-102.5° C.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationthe precipitate was filtered off
  3. washwashed with a little cold petroleum ether
  4. customdried under vacuum at room temperature

Sources & evidence

ORD record
ord-901b5117603e4f17a2087ef93fa539c8
Source dataset
uspto-grants-1984_09
Patent number
US04472400

Reaction notes

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