Triethylamine → HCID 59457473, compound

HRID 1710755Notes

Reaction equation

HRID 1710755 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[O:13][C:14]([C:18]([OH:20])=O)=[C:15]([CH3:17])[N:16]=2)=[CH:8][CH:7]=1.C(N(CC)CC)C.S(Cl)(Cl)=O.[CH:32]1([CH2:35][NH:36][CH2:37][CH2:38][CH3:39])[CH2:34][CH2:33]1>C(Cl)(Cl)Cl>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[O:13][C:14]([C:18]([N:36]([CH2:35][CH:32]3[CH2:34][CH2:33]3)[CH2:37][CH2:38][CH3:39])=[O:20])=[C:15]([CH3:17])[N:16]=2)=[CH:10][CH:11]=1

Participants

6

Reactant 4

HCID 8471Triethylamine2×HCID 24386Thionyl ChlorideHCID 117787Cyclopropanemethanamine, N-propyl-HCID 59457455HCID 59457455, compound

Product 1

HCID 59457473HCID 59457473, compoundYield 97%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
0 °C

Procedure

A mixture of 2-[4-(3-chloropropoxy)phenyl]-4-methyl-1,3-oxazole-5-carboxylic acid i43 (3.18 g, 10.75 mmol, 1 eq) and triethylamine (1.5 ml, 10.75 mmol, 1 eq) in chloroform (70 ml) is cooled to 0° C. Thionyl chloride (2.3 ml, 32 mmol, 3 eq) is then added dropwise. The mixture is refluxed for 2 h 30 and the solvent is evaporated. The residue is taken up in cold dichloromethane (20 ml, 0° C.) and treated with triethylamine (0.6 ml, 4.3 mmol, 2 eq) and N-(cyclopropylmethyl)propan-1-amine (0.29 g, 2.58 mmol, 1.2 eq). The mixture is stirred at room temperature overnight and then washed two times with a saturated solution of aqueous ammonium chloride. The organic layer is dried over magnesium sulfate, filtered and concentrated under vacuum to give 0.82 g of 2-[4-(3-chloropropoxy)phenyl]-N-(cyclopropylmethyl)-4-methyl-N-propyl-1,3-oxazole-5-carboxamide i44.

Workup

  1. temperatureThe mixture is refluxed for 2 h 30
  2. customthe solvent is evaporated
  3. customis taken up in cold dichloromethane (20 ml, 0° C.)
  4. washwashed two times with a saturated solution of aqueous ammonium chloride
  5. dry with materialThe organic layer is dried over magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-ea8d5e15d1904c71960d34347cf1fb7b
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

Loading…