Chloroacetyl chloride → N-[1-(6-Bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethyl]-2-chloro-acetamide

HRID 538305Notes

Reaction equation

HRID 538305 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH2:19])([CH2:14][O:15][CH2:16][O:17][CH3:18])[CH2:9][O:10][CH2:11][O:12][CH3:13])[CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:26][CH2:27][C:28](Cl)=[O:29]>C(Cl)Cl>[Br:1][C:2]1[N:7]=[C:6]([C:8]([NH:19][C:28](=[O:29])[CH2:27][Cl:26])([CH2:9][O:10][CH2:11][O:12][CH3:13])[CH2:14][O:15][CH2:16][O:17][CH3:18])[CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 866680191-(6-Bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethylamine

Product 1

HCID 86668020N-[1-(6-Bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethyl]-2-chloro-acetamide

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 1-(6-bromo-pyridin-2-yl)-2-methoxymethoxy-1-methoxymethoxymethyl-ethylamine (15.0 g, 44.75 mmol) in DCM (150 ml) was added aqueous Na2CO3 solution (10.91 g, 102.925 mmmol in water, 30 ml) was added at 0° C. and stirred for 10 min. Chloroacetylchloride (5.56 g, 49.225 mmol) was added to the resultant reaction mixture at 0° C. stirring continued for 1 h at ambient temperature. Reaction mixture was diluted with DCM (˜1 l), and worked up the reaction mixture by washing with water, brine and dried over anhy. Na2SO4. Organic layer was separated and concentrated under reduced pressure to obtain title compound as a brown liquid. Yield=9.0 g (48%). TLC (50% ethyl acetate in hexane) Rf=0.54; LCMS: RtH7=1.341, [M+1]=411.0 and 413.0; HPLC: RtH9=4.27 min (50.4%); 1H NMR (400 MHz, CDCl3): δ 8.11 (d, 1H), 7.57-7.52 (m, 1H), 7.46-7.37 (m, 2H), 4.59-4.52 (m, 4H), 4.23-4.17 (m, 4H), 4.09-4.04 (m, 2H), 3.21 (s, 6H).

Workup

  1. additionwas added at 0° C.
  2. customreaction mixture at 0° C.
  3. stirringstirring
  4. waitcontinued for 1 h at ambient temperature
  5. customReaction mixture
  6. washby washing with water, brine
  7. customdried over anhy
  8. customOrganic layer was separated
  9. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-9142c04097fb44aa83b03cea94b2d0e0
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

Loading…