Dichloromethane → HCID 58932626, compound

HRID 853833Notes

Reaction equation

HRID 853833 reaction equation
[Cl:1][C:2]1[C:18]([Cl:19])=[CH:17][C:5]2[N:6]([CH2:9][CH:10]([OH:16])[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[CH:7]=[N:8][C:4]=2[CH:3]=1.C(Cl)Cl.Cl[C:24]([O:26][C:27]1[CH:32]=[CH:31][C:30]([N+:33]([O-:35])=[O:34])=[CH:29][CH:28]=1)=[O:25]>N1C=CC=CC=1.C(OCC)(=O)C>[C:24](=[O:25])([O:26][C:27]1[CH:28]=[CH:29][C:30]([N+:33]([O-:35])=[O:34])=[CH:31][CH:32]=1)[O:16][CH:10]([CH2:9][N:6]1[C:5]2[CH:17]=[C:18]([Cl:19])[C:2]([Cl:1])=[CH:3][C:4]=2[N:8]=[CH:7]1)[CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13]

Participants

6

Reactant 3

HCID 6344DichloromethaneHCID 821294-Nitrophenyl chloroformateHCID 58932639HCID 58932639, compound

Product 1

HCID 58932626HCID 58932626, compoundYield 77%

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
80 °C

Procedure

The product from step B (445 mg, 1.48 mmol) was dissolved in pyridine (4 mL) and CH2Cl2 (2 mL) and treated with 4-nitrophenyl chloroformate (328 mg, 1.62 mmol). The reaction vessel was sealed and heated to 80° C. overnight. After cooling to room temperature, the reaction was diluted with ethyl acetate and extracted with water twice, 1 M aqueous HCl 3 times, water once and saturated aqueous NaCl once. The organics were then dried over MgSO4 and the solvent was removed. The residue was treated with ether, heated to reflux and put in the refrigerator overnight at −10° C. The resulting solid was collected, washed with cold ether and dried to afford 531 mg (77%) of the product as a slightly colored solid: 1H NMR (DMSO, 400 MHz) δ 1.01 (s, 9H), 1.66-1.79 (m, 2H), 4.62 (dd, 1H, J=8.2, J2=14.9), 4.70 (dd, 1H, J=3.4, J2=14.9), 5.23-5.32 (m, 1H), 7.11-7.17 (m, 2H), 8.03 (s, 1H), 8.21 (s, 1H), 8.28-8.33 (m, 2H), 8.51 (s, 1H); HPLC-MS calcd. for C21H22Cl2N4O2 (M+H+) 466.1, found 466.3.

Workup

  1. customThe reaction vessel was sealed
  2. temperatureAfter cooling to room temperature
  3. extractionextracted with water twice
  4. dry with materialThe organics were then dried over MgSO4
  5. customthe solvent was removed
  6. additionThe residue was treated with ether
  7. temperatureheated
  8. temperatureto reflux
  9. customput in the refrigerator overnight at −10° C
  10. customThe resulting solid was collected
  11. washwashed with cold ether
  12. customdried

Sources & evidence

ORD record
ord-c39a2cd6ed774e01a33ae63bbddfe77a
Source dataset
uspto-grants-2007_08
Patent number
US07256207B2

Reaction notes

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