Chloroacetyl chloride → HCID 22058519, compound

HRID 1826931Notes

Reaction equation

HRID 1826931 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)=[C:4]([O:13][CH3:14])[CH:3]=1.C(N(CC)CC)C.[Cl:22][CH2:23][C:24](Cl)=[O:25]>ClCCl>[Cl:22][CH2:23][C:24]([NH:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:12][CH:11]=[N:10][CH:9]=2)=[C:4]([O:13][CH3:14])[CH:3]=1)=[O:25]

Participants

5

Reactant 3

HCID 6577Chloroacetyl chlorideHCID 8471TriethylamineHCID 154627323-Methoxy-4-(oxazol-5-yl)aniline

Product 1

HCID 22058519HCID 22058519, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 1D (500 mg, 2.63 mmol) and triethylamine (370 μL, 2.89 mmol) in dichloromethane (13.0 mL), was added chloroacetyl chloride (0.23 mL, 2.89 mmol) at 0° C. The reaction mixture was stirred at 0° C. for 10 min. and then at RT for 4 h. The mixture eas diluted with dichloromathane, washed with water, brine, and dried over Na2SO4. The mixture was filtered through celite and concentrated in vacuo to give 2A as a yellow solid. LC/MS: ret. timeA=3.123 min., MS (M+H)+=267.

Workup

  1. waitat RT for 4 h
  2. additionThe mixture eas diluted with dichloromathane
  3. washwashed with water, brine
  4. dry with materialdried over Na2SO4
  5. filtrationThe mixture was filtered through celite and
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-3a7ed9570a754ecb936fcc6d91a18c12
Source dataset
uspto-grants-2006_05
Patent number
US07053111B2

Reaction notes

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