Triethylamine → HCID 385601, compound

HRID 988616Notes

Reaction equation

HRID 988616 reaction equation
[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]([NH:11][C:12]2[CH:20]=[CH:19][CH:18]=[CH:17][C:13]=2[C:14]([OH:16])=[O:15])=O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].C(Cl)(=O)C(Cl)=O.C(N(CC)CC)C>CN(C=O)C.C(Cl)Cl>[C:1]([C:5]1[CH:22]=[CH:21][C:8]([C:9]2[O:15][C:14](=[O:16])[C:13]3[CH:17]=[CH:18][CH:19]=[CH:20][C:12]=3[N:11]=2)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 765906HCID 765906, compound

Product 1

HCID 385601HCID 385601, compoundYield 96.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent2×

Procedure

To a stirring mixture of the 2-(4-tert-butylbenzoylamino)benzoic acid (9.5 g, 32 mmol), CH2Cl2 (200 mL) and 2 drops of DMF was added 2 M oxalyl chloride in CH2Cl2 (19 mL). After stirring at ambient temperature for 45 minutes, the mixture was concentrated under vacuum to an oil, redissolved in 100 mL CH2Cl2 and cooled to 0° C. To this was added triethylamine (3.3 g, 33 mmol) at 0° C. for 1 hour. The solvent was removed in vacuo and the residue purified by flash chromatrography using hexanes/EtOAc to give 8.6 g (96%) of a white powder.

Workup

  1. concentrationthe mixture was concentrated under vacuum to an oil
  2. dissolutionredissolved in 100 mL CH2Cl2
  3. temperaturecooled to 0° C
  4. customThe solvent was removed in vacuo
  5. customthe residue purified by flash chromatrography

Sources & evidence

ORD record
ord-210cd2ad547a49bc9255fc0b6d1a7d11
Source dataset
uspto-grants-2003_10
Patent number
US06635657B1

Reaction notes

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