Triethylamine → HCID 15269401, compound

HRID 580972Notes

Reaction equation

HRID 580972 reaction equation
C(N(CC)CC)C.[I:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](Cl)=[O:14])=[CH:11][CH:10]=1.Cl.[CH3:19][O:20][C:21](=[O:24])[CH2:22][NH2:23]>ClCCl>[I:8][C:9]1[CH:17]=[CH:16][C:12]([C:13](=[O:14])[NH:23][CH2:22][C:21]([O:20][CH3:19])=[O:24])=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743734-Iodobenzoyl chlorideHCID 122755Glycine methyl ester hydrochloride

Product 1

HCID 15269401HCID 15269401, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Conditions

Temperature
5 °C

Procedure

Triethylamine (5.4 ml) was added to a solution of 4-iodobenzoyl chloride (5.06 g) in dichloromethane (30 ml) at 5° C. Glycine methyl ester hydrochloride (2.4 g) was then added to the reaction mixture and the mixture was stirred at 5° C. for 2 hours. The mixture was then stirred at ambient temperature overnight. Dichloromethane (100 ml) was added and the mixture was washed with water (2×100 ml), dried (MgSO4) and evaported. The residue was triturated with pentane to give a solid which was collected by filtration to give methyl 4-iodohippurate, m.p. 166-168° C. NMR: 3.65(3H,s), 4.0(2H,d), 7.65(2H,m), 7.88(2H,m) and 9.0(1H,m); m/z 320(M+H).

Workup

  1. stirringThe mixture was then stirred at ambient temperature overnight
  2. washthe mixture was washed with water (2×100 ml)
  3. dry with materialdried (MgSO4)
  4. customThe residue was triturated with pentane
  5. customto give a solid which
  6. filtrationwas collected by filtration

Sources & evidence

ORD record
ord-adb78aa6ae9147458fbb5791ce6210ba
Source dataset
uspto-grants-1999_07
Patent number
US05919793

Reaction notes

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