Chloroacetyl chloride → HCID 86668044, compound

HRID 538334Notes

Reaction equation

HRID 538334 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([NH2:16])[CH2:13][O:12][C:11]([CH3:15])([CH3:14])[O:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:23][CH2:24][C:25](Cl)=[O:26]>C(Cl)Cl>[Br:1][C:2]1[CH:7]=[C:6]([C:8]2([NH:16][C:25](=[O:26])[CH2:24][Cl:23])[CH2:13][O:12][C:11]([CH3:14])([CH3:15])[O:10][CH2:9]2)[CH:5]=[CH:4][N:3]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 10340Sodium CarbonateHCID 86668043HCID 86668043, compound

Product 1

HCID 86668044HCID 86668044, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-(2-bromo-pyridin-4-yl)-2,2-dimethyl-[1,3]dioxan-5-ylamine (9.5 g, 33.1 mmol) in DCM (100 ml) was added aq. Na2CO3 (8.7 g in 50 ml) at 0° C. and stirring continued for 5 min. Chloroacetyl chloride (2.9 ml, 36.41 mmol) was added to the resultant reaction mixture drop wise and stirred for 30 min at 0° C. Reaction mass was diluted with DCM (200 ml) and organic layer was washed successively washed with water, brine, dried over anhydrous Na2SO4 and concentrated under reduced pressure to obtain brown solid. The product was directly used in the next step with further purification. Yield=10.2 g (85%). TLC (50% ethyl acetate in hexane) Rf=0.15; LCMS: RtH8=0.55 [M+1]+=363.0 and 364.9.

Workup

  1. customreaction mixture drop wise
  2. stirringstirred for 30 min at 0° C
  3. customReaction mass
  4. washwas washed successively
  5. washwashed with water, brine
  6. dry with materialdried over anhydrous Na2SO4
  7. concentrationconcentrated under reduced pressure
  8. customto obtain brown solid
  9. customThe product was directly used in the next step with further purification

Sources & evidence

ORD record
ord-7293a68a664647eea8177b780149b0cf
Source dataset
uspto-grants-2014_10
Patent number
US08865712B2

Reaction notes

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