Triethylamine → HCID 67257805, compound

HRID 713824Notes

Reaction equation

HRID 713824 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][NH:11][C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:4]=2[O:3][CH2:2]1.C(N(CC)CC)C.[Br:32][CH2:33][C:34](Cl)=[O:35]>C(Cl)Cl>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[C:9]([CH2:10][N:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[O:18][C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:34](=[O:35])[CH2:33][Br:32])[C:4]=2[O:3][CH2:2]1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 89602Bromoacetyl chloride2×HCID 67258841HCID 67258841, compound

Product 1

HCID 67257805HCID 67257805, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of N-(benzo[1,3]dioxol-4-ylmethyl)-N-(2-phenyloxy-phenyl)amine (0.18 g, 0.58 mmol) dissolved in DCM (4 mL) was added triethylamine (0.24 g, 2.32 mmol, 0.32 mL). The reaction was cooled to 0° C. and bromoacetyl chloride (0.18 g, 1.16 mmol, 0.10 mL) was added. The mixture was stirred at room temperature for 2 h. LC-MS indicated starting material and product (1:1). Further triethylamine (0.24 g, 2.32 mmol, 0.32 mL) and bromoacetyl chloride (0.18 g, 1.16 mmol, 0.10 mL) were added and stirred at room temperature for 2 h. The solvents were removed in vacuo, the residue quenched with water (10 mL), extracted with DCM (2×20 mL), dried over MgSO4, filtered and solvents removed in vacuo. The crude material was purified by silica gel chromatography eluting with DCM (A) and MeOH (B) (1% B, 80 g, 2 CV, 60 mL/min). The impure product was further purified by silica gel chromatography eluting with DCM (A) and EtOAc (B) (1-5% B, 80 g, 4.5 CV, 60 mL/min) to afford 120 mg (47%) of N-(benzo[1,3]dioxol-4-ylmethyl)-2-Bromo-N-(2-phenyloxy-phenyl)acetamide as a colourless oil.

Workup

  1. stirringstirred at room temperature for 2 h
  2. customThe solvents were removed in vacuo
  3. customthe residue quenched with water (10 mL)
  4. extractionextracted with DCM (2×20 mL)
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. customsolvents removed in vacuo
  8. customThe crude material was purified by silica gel chromatography
  9. washeluting with DCM (A) and MeOH (B) (1% B, 80 g, 2 CV, 60 mL/min)
  10. customThe impure product was further purified by silica gel chromatography
  11. washeluting with DCM (A) and EtOAc (B) (1-5% B, 80 g, 4.5 CV, 60 mL/min)

Sources & evidence

ORD record
ord-f2d77fee84434e7287bcb7941690b2ca
Source dataset
uspto-grants-2015_11
Patent number
US09186424B2

Reaction notes

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