Triethylamine → HCID 16098369, compound

HRID 488582Notes

Reaction equation

HRID 488582 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH:9]([C:13]2[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=2)[C:10](O)=[O:11])=[CH:4][CH:3]=1.C(Cl)(=O)C(Cl)=O.Cl.[CH3:26][O:27][NH:28][CH3:29].C(N(CC)CC)C>C(Cl)Cl.CCOCC.CN(C)C=O>[CH3:26][O:27][N:28]([CH3:29])[C:10](=[O:11])[CH:9]([C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH2:8][C:5]1[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 222705593-(4-Chlorophenyl)-2-phenylpropanoic acid

Product 1

HCID 16098369HCID 16098369, compound

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 3-(4-chlorophenyl)-2-phenylpropionic acid (Step B, 14 g, 55 mmol) in CH2Cl2 (125 mL) at 0° C. was added dimethyl formamide (50 μL) and oxalyl chloride (14 g, 0.11 mol) dropwise. The reaction was allowed to warm to room temperature overnight and concentrated to dryness to give the crude acyl chloride, which was used without further purification. Thus, to a solution of the acyl chloride in CH2Cl2 (250 mL) was added N-methoxy-N-methylamine hydrochloride (11 g, 0.11 mol) and triethyl amine (dried over activated molecular sieves, 30 mL, 0.22 mol) at 0° C. After stirring at room temperature for 4 h, the reaction mixture was diluted with ether (500 mL) and successively washed with water, dilute aqueous sodium hydrogen sulfate and brine, dried over anhydrous MgSO4, filtered, and concentrated to dryness to give the crude product, which was used without further purification. 1H NMR (500 MHz, CD3OD): δ 7.4-7.1 (m, 9H), 4.38 (br, 1H), 3.48 (s, 3H), 3.35 (dd, 1H), 3.10 (s, 3H), 2.92 (dd, 1H); LC-MS: m/e 304 (3.6 min).

Workup

  1. concentrationconcentrated to dryness
  2. customto give the crude acyl chloride, which
  3. customwas used without further purification
  4. washsuccessively washed with water, dilute aqueous sodium hydrogen sulfate and brine
  5. dry with materialdried over anhydrous MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-608323aa2d7a48e6a1a95d1e7ad9c38f
Source dataset
uspto-grants-2005_12
Patent number
US06972295B2

Reaction notes

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