Tert-Butylamine → HCID 602510, compound

HRID 1422361Notes

Reaction equation

HRID 1422361 reaction equation
[C:1]1([C:16]2C=CC=CC=2)[CH:6]=[CH:5][C:4]([C:7]2[C:12](C(O)=O)=[CH:11][CH:10]=[CH:9][CH:8]=2)=[CH:3][CH:2]=1.C(Cl)(=O)C(Cl)=[O:24].[C:28]([NH2:32])([CH3:31])([CH3:30])[CH3:29].CCN(CC)CC>CN(C=O)C.CN(C1C=CN=CC=1)C.C(Cl)(Cl)Cl.C(Cl)Cl>[C:28]([NH:32][C:16]([C:1]1[CH:2]=[CH:3][C:4]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[CH:5][CH:6]=1)=[O:24])([CH3:31])([CH3:30])[CH3:29]

Participants

9

Reactant 4

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 13629282HCID 13629282, compound

Product 1

HCID 602510HCID 602510, compound

Reagents, catalysts & solvents 4

HCID 6228DimethylformamideCatalystHCID 142844-(Dimethylamino)pyridineCatalystHCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 1 L round bottomed flask with a stirring bar and a drying tube was added 4-biphenylbenzoic acid (35.14 g, 177.26 mmol), CH2Cl2 (500 mL) and oxalyl chloride (17.18 mL, 196.96 mmol). To this well stirred mixture was added 10 drops of DMF. This mixture was stirred at ambient temperature for 5 h. The solvent and excess oxalyl chloride were removed in vacuo and the solid acid chloride was redissolved in fresh CH2Cl2 (500 mL). This solution was cooled to 0° C. and tert-butylamine (23.28 mL, 221.58 mmol), Et3N (30.88 mL, 221.58 mmol) and 4-DMAP (0.20 g) were added sequentially. The cooling bath was allowed to expire and the mixture was stirred at ambient temperature for 18 h. The reaction mixture was diluted with an equal volume of CHCl3 and this solution was washed successively with 1N HCl, NaHCO3 solution and brine. Drying (MgSO4), filtration and removal of the solvent in vacuo gave an off white solid. This material was triturated with Et2O (100 mL) and collected on a frit and dried in vacuo to afford the title compound.

Workup

  1. stirringThis mixture was stirred at ambient temperature for 5 h
  2. customThe solvent and excess oxalyl chloride were removed in vacuo
  3. dissolutionthe solid acid chloride was redissolved in fresh CH2Cl2 (500 mL)
  4. stirringthe mixture was stirred at ambient temperature for 18 h
  5. washthis solution was washed successively with 1N HCl, NaHCO3 solution and brine
  6. customDrying
  7. filtration(MgSO4), filtration and removal of the solvent in vacuo
  8. customgave an off white solid
  9. customThis material was triturated with Et2O (100 mL)
  10. customcollected on a frit
  11. customdried in vacuo

Sources & evidence

ORD record
ord-ca47f67b323e4badb6905f95beca98e2
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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