Chloroacetyl chloride → 2-chloro-N,N-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]acetamide

HRID 2356337

Reaction equation

HRID 2356337 reaction equation
[Cl:1][CH2:2][C:3](Cl)=[O:4].[NH:6]([CH2:20][CH2:21][N:22]1[C:30](=[O:31])[C:29]2[C:24](=[CH:25][CH:26]=[CH:27][CH:28]=2)[C:23]1=[O:32])[CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19].CCN(CC)CC>C(Cl)Cl>[Cl:1][CH2:2][C:3]([N:6]([CH2:7][CH2:8][N:9]1[C:17](=[O:18])[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[C:10]1=[O:19])[CH2:20][CH2:21][N:22]1[C:23](=[O:32])[C:24]2[C:29](=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:30]1=[O:31])=[O:4]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 3547072,2'-[iminobis(ethane-2,1-diyl)]bis(1H-isoindole-1,3(2H)-dione)

Product 1

HCID 684562152-chloro-N,N-bis[2-(1,3-dioxo-1,3-dihydro-2H-isoindol-2-yl)ethyl]acetamideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution chloroacetyl chloride (1.2 mL, 15.2 mmol) in DCM (65 mL) at 0° C. was added dropwise a solution of 2,2′-(iminodi-2,1-ethanediyl)bis(1H-isoindole-1,3(2H)-dione) (5 g, 13.7 mmol) [prepared according to Anelli, P. L.; et. al. J. Org. Chem. 1984 49, 4197.] and Et3N (2.5 mL, 17.9 mmol) in DCM (65 mL). After 1 h, the solution was partitioned between H2O-DCM and the aqueous phase was washed several times with DCM. The combined organic fractions were dried (Na2SO4), concentrated and purified via column chromatography (silica, 5% MeOH in DCM (NH4OH)) yielding the title compound (5.9 g, 98%) as a yellow foam: LCMS (ES) m/e 440 (M+H)+.

Workup

  1. customthe solution was partitioned between H2O-DCM
  2. washthe aqueous phase was washed several times with DCM
  3. dry with materialThe combined organic fractions were dried (Na2SO4)
  4. concentrationconcentrated
  5. custompurified via column chromatography (silica, 5% MeOH in DCM (NH4OH))

Sources & evidence

ORD record
ord-d5d3d71e83aa439296bf223a02be8b87
Source dataset
uspto-grants-2010_07
Patent number
US07759340B2

Linked notes

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