Tert-Butylamine → HCID 68387256, compound

HRID 1522760Notes

Reaction equation

HRID 1522760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[CH2:13][C:12]([CH3:17])([C:14]([OH:16])=O)[O:11][N:10]=2)[CH:5]=[C:6]([Cl:8])[CH:7]=1.C(Cl)(=O)C(Cl)=O.[C:24]([NH2:28])([CH3:27])([CH3:26])[CH3:25].C(N(CC)CC)C.CN(C1C=CC=CN=1)C>C(Cl)Cl.CN(C)C=O>[C:24]([NH:28][C:14]([C:12]1([CH3:17])[O:11][N:10]=[C:9]([C:4]2[CH:5]=[C:6]([Cl:8])[CH:7]=[C:2]([Cl:1])[CH:3]=2)[CH2:13]1)=[O:16])([CH3:27])([CH3:26])[CH3:25]

Participants

8

Reactant 5

HCID 6385Tert-ButylamineHCID 8471TriethylamineHCID 218852-DimethylaminopyridineHCID 65578Oxalyl chlorideHCID 683870031401093-84-2

Product 1

HCID 68387256HCID 68387256, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent3×

Procedure

100 ml of CH2Cl2 and 70 mg of dimethylformamide were added to 5.00 g (18.2 mmol) of 3-(3,5-dichlorophenyl)-5-methyl-4,5-dihydro-1,2-oxazole-5-carboxylic acid. At RT, 3.47 g (27.4 mmol) of oxalyl chloride were added slowly with stirring. After 30 min, the solution was concentrated and used without further purification (crude yield 5.50 g). 200 mg (0.68 mmol) of this crude product were taken up in 3 ml CH2Cl2 and added dropwise to a solution of 50 mg (0.68 mmol) of tert butylamine, 69 mg (0.68 mmol) of triethylamine and 10 mg of dimethylaminopyridine in 50 ml of CH2Cl2 at C. For work-up, the mixture was extracted with water, with saturated NaHCO3 solution and once more with water. Drying of the organic phases, filtration and removal of the solvent under reduced pressure gave the product.

Workup

  1. concentrationthe solution was concentrated
  2. customused without further purification (crude yield 5.50 g)
  3. extractionFor work-up, the mixture was extracted with water, with saturated NaHCO3 solution and once more with water
  4. customDrying of the organic phases, filtration and removal of the solvent under reduced pressure
  5. customgave the product

Sources & evidence

ORD record
ord-042204115f0d417692a9f7c8bb1ba053
Source dataset
uspto-grants-2015_07
Patent number
US09078442B2

Reaction notes

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