Chloroacetyl chloride → HCID 68749928, compound

HRID 624223Notes

Reaction equation

HRID 624223 reaction equation
[OH:1]/[N:2]=[C:3](/[C:5]1[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]2[CH2:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[CH2:15]2)=[O:13])=[CH:7][CH:6]=1)\[NH2:4].C(=O)([O-])[O-].[K+].[K+].[Cl:29][CH2:30][C:31](Cl)=O>CC(C)=O>[Cl:29][CH2:30][C:31]1[O:1][N:2]=[C:3]([C:5]2[CH:10]=[CH:9][C:8]([NH:11][C:12]([N:14]3[CH2:15][C:16]4[C:21](=[CH:20][CH:19]=[CH:18][CH:17]=4)[CH2:22]3)=[O:13])=[CH:7][CH:6]=2)[N:4]=1

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 11430Potassium CarbonateHCID 87561227HCID 87561227, compound

Product 1

HCID 68749928HCID 68749928, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

To a 25 mL round-bottomed flask containing (Z)—N-(4-(N′-hydroxycarbamimidoyl)phenyl)isoindoline-2-carboxamide (1.5 g, 5.06 mmol) in acetone (5 ml) was added potassium carbonate (7.00 g, 50.6 mmol) in a single portion. The reaction mixture was cooled to 0° C. and 2-chloroacetyl chloride (3.22 ml, 40.5 mmol) was added slowly. The resulting mixture was warmed to room temperature and stirred for two hours. The solvent was removed and the solid was triturated with water and then filtered with water washes. The dried solid was dissolved in DMF, heated to 100° C. and stirred for two hours. Work-up with water and dichlormethane followed by chromatography provided the title compound.

Workup

  1. temperatureThe resulting mixture was warmed to room temperature
  2. customThe solvent was removed
  3. customthe solid was triturated with water
  4. filtrationfiltered with water washes
  5. dissolutionThe dried solid was dissolved in DMF
  6. temperatureheated to 100° C.
  7. stirringstirred for two hours

Sources & evidence

ORD record
ord-a9f9f105ad694f68b7458c283ab6bed5
Source dataset
uspto-grants-2016_04
Patent number
US09302989B2

Reaction notes

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