Acetic Anhydride → HCID 11711491, compound

HRID 272301Notes

Reaction equation

HRID 272301 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]3[C:12]([N:15]4[CH2:20][CH2:19][CH:18]([C:21]5[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=5)[CH2:17][CH2:16]4)=[N:13][N:14]=[C:10]3[CH2:9][NH:8][CH2:7][C:6]=2[CH:27]=1.C(N(CC)CC)C.[C:35](OC(=O)C)(=[O:37])[CH3:36]>ClCCl.O>[C:35]([N:8]1[CH2:7][C:6]2[CH:27]=[C:2]([Cl:1])[CH:3]=[CH:4][C:5]=2[N:11]2[C:12]([N:15]3[CH2:20][CH2:19][CH:18]([C:21]4[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=4)[CH2:17][CH2:16]3)=[N:13][N:14]=[C:10]2[CH2:9]1)(=[O:37])[CH3:36]

Participants

6

Reactant 3

HCID 7918Acetic AnhydrideHCID 8471TriethylamineHCID 11696573HCID 11696573, compound

Product 1

HCID 11711491HCID 11711491, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a stirred solution of the compound from example 5 (200 mg, 0.53 mmol) in dichloromethane (5 mL) was added triethylamine (110 μL, 0.79 mmol). The solution was cooled to 0° C. and acetic anhydride (59.6 μL, 0.63 mmol) was added. The reaction mixture was then stirred for 1 hour, before it was diluted with water (10 mL) and the phases were separated. The organic phase was washed with brine (10 mL), dried over magnesium sulfate and concentrated in vacuo. The residue was azeotroped with ethyl acetate to give the product as a white, crystalline solid, 206 mg (93%)

Workup

  1. customthe phases were separated
  2. washThe organic phase was washed with brine (10 mL)
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated in vacuo
  5. customThe residue was azeotroped with ethyl acetate
  6. customto give the product as a white, crystalline solid, 206 mg (93%)

Sources & evidence

ORD record
ord-abb383fb3f4a4fb28908d0de9bbf429f
Source dataset
uspto-grants-2008_11
Patent number
US07456170B2

Reaction notes

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