Triethylamine → HCID 57837977, compound

HRID 732125Notes

Reaction equation

HRID 732125 reaction equation
[Cl:1][CH:2]([CH3:7])[C:3]([NH:5][OH:6])=[NH:4].C(N(CC)CC)C.[CH3:15][C:16]1[CH:17]=[C:18]([CH:22]=[CH:23][CH:24]=1)[C:19](Cl)=O>C(Cl)Cl>[Cl:1][CH:2]([C:3]1[N:4]=[C:15]([C:16]2[CH:17]=[C:18]([CH3:19])[CH:22]=[CH:23][CH:24]=2)[O:6][N:5]=1)[CH3:7]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 743753-Methylbenzoyl chlorideHCID 178456129HCID 178456129, compound

Product 1

HCID 57837977HCID 57837977, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
120 °C

Procedure

2-Chloro-N-hydroxy-propionamidine (218 mg, 1.78 mmol) and triethylamine (0.677 ml, 4.86 mmol) were added to 3-methyl-benzoyl chloride (250 mg, 1.62 mmol) in DCM (10.0 ml) at 0° C. and the resulting mixture was stirred for 20 min. The solution was concentrated and DMF (20 ml) was added to the residue and heated at 120° C. for 20 min. The product was purified by flash chromatography using 10-20% EA in hex. affording 0.250 g (59% yield over 2 steps) of the title compound.

Workup

  1. concentrationThe solution was concentrated
  2. additionDMF (20 ml) was added to the residue
  3. customThe product was purified by flash chromatography

Sources & evidence

ORD record
ord-c7295e1118bf4491bd884c693227c104
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

Loading…