Dichloromethane → N-[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-acetamide

HRID 747199Notes

Reaction equation

HRID 747199 reaction equation
[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10](NC)[O:9][N:8]=2)=[CH:4][CH:3]=1.[CH2:14]([N:16]([CH2:19]C)CC)[CH3:15].ClCCl.C(Cl)(=[O:26])C>C(OCC)(=O)C>[Br:1][C:2]1[S:6][C:5]([C:7]2[CH2:11][CH:10]([CH2:19][NH:16][C:14](=[O:26])[CH3:15])[O:9][N:8]=2)=[CH:4][CH:3]=1

Participants

6

Reactant 4

HCID 6344DichloromethaneHCID 6367Acetyl chlorideHCID 8471TriethylamineHCID 17954483[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-yl]-methylamine

Product 1

HCID 59749420N-[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-ylmethyl]-acetamideYield 49.5%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Conditions

Temperature
0 °C

Procedure

[3-(5-Bromo-thien-2-yl)-4,5-dihydro-isoxazol-5-yl]-methylamine (2.1 g, 8 mmol) and triethylamine (1.7 ml, 12 mmol) were added to anhydrous dichloromethane (50 ml) and cooled to 0° C. Acetyl chloride (0.670 ml, 9.6 mmol) was then added dropwise and the reaction was stirred for 3 hours followed by addition of ethyl acetate (100 ml). The precipitate was collected and washed with water (2×25 ml) to give the desired product (1.2 g).

Workup

  1. customThe precipitate was collected
  2. washwashed with water (2×25 ml)

Sources & evidence

ORD record
ord-ce0514f4b803414a87cf4dbfd8033cbf
Source dataset
uspto-grants-2008_07
Patent number
US07396847B2

Reaction notes

Loading…