Triethylamine → HCID 67351355, compound

HRID 1669968Notes

Reaction equation

HRID 1669968 reaction equation
[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH2:10].C(N(CC)CC)C.[CH2:19]([O:26][C:27]1[CH:35]=[CH:34][C:30]([C:31](Cl)=[O:32])=[CH:29][CH:28]=1)[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1>ClCCl>[CH3:1][O:2][C:3](=[O:11])[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[NH:10][C:31](=[O:32])[C:30]1[CH:29]=[CH:28][C:27]([O:26][CH2:19][C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)=[CH:35][CH:34]=1

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8635Methyl AnthranilateHCID 37664104-Benzyloxybenzoylchloride

Product 1

HCID 67351355HCID 67351355, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To 2-amino-benzoic acid methyl ester (0.51 mL) and triethylamine (0.69 mL) in dichloromethane (31 mL) at −50° C. was slowly added a solution of 4-benzyloxy-benzoyl chloride [1486-50-6] (1 g) in 31 mL of dichloromethane. The reaction mixture was then allowed to warm up to room temperature and stirred for an additional hour. After such time, the reaction mixture was washed with water. The aqueous phase was further extracted with dichloromethane. The combined organic phases were dried over sodium sulfate and concentrated in vacuo. The residue was purified by column chromatography (heptane-ethyl acetate: 0-50%) to yield 2-(4-benzyloxy-benzoylamino)-benzoic acid methyl ester (400 mg). MS (m/e): 362.5 (M+H+, 100%).

Workup

  1. washAfter such time, the reaction mixture was washed with water
  2. extractionThe aqueous phase was further extracted with dichloromethane
  3. dry with materialThe combined organic phases were dried over sodium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by column chromatography (heptane-ethyl acetate: 0-50%)

Sources & evidence

ORD record
ord-0c7903d7373d4a3182b5150840125ca2
Source dataset
uspto-grants-2011_08
Patent number
US07989657B2

Reaction notes

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