Chloroacetyl chloride → HCID 131732690, compound

HRID 1466166Notes

Reaction equation

HRID 1466166 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([NH:11][CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:20])([CH3:19])[CH3:18])[CH2:5]2.[Cl:22][CH2:23][C:24](Cl)=[O:25]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[CH2:7][CH:6]([N:11]([C:24](=[O:25])[CH2:23][Cl:22])[CH2:12][CH2:13][NH:14][C:15](=[O:21])[O:16][C:17]([CH3:18])([CH3:20])[CH3:19])[CH2:5]2

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 131732689tert-Butyl {2-[(5-bromo-2,3-dihydro-1H-inden-2-yl)amino]ethyl}carbamate

Product 1

HCID 131732690HCID 131732690, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of tert-Butyl {2-[(5-bromo-2,3-dihydro-1H-inden-2-yl)amino]ethyl}carbamate (140 mg, 0.39 mmol) in 10 mL of DCM was added TEA (159 mg, 1.58 mmol) and chloroacetyl chloride (49 mg, 0.43 mmol) at 0° C. The mixture was stirred at RT for 2 hours. DCM was added to the mixture, and then washed 1N HCl and brine. The organic layer was dried over anhydrous Na2SO4 and concentrated. The residue was used directly in next step.

Workup

  1. washwashed 1N HCl and brine
  2. dry with materialThe organic layer was dried over anhydrous Na2SO4
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-54b8bfc658fa4109b3f5680cfc35e479
Source dataset
uspto-grants-2015_04
Patent number
US08999990B2

Reaction notes

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