Triethylamine → HCID 59701085, compound

HRID 902050Notes

Reaction equation

HRID 902050 reaction equation
Cl.Cl.[NH:3]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[CH:6]([NH:13][O:14][CH2:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH2:5][NH:4]1.C(N(CC)CC)C.[O:29]=[C:30](Cl)OC(Cl)(Cl)Cl.CN(C1C=CC=CN=1)C>C(#N)C>[O:29]=[C:30]1[N:13]([O:14][CH2:15][C:16]([O:18][CH2:19][CH:20]=[CH2:21])=[O:17])[CH:6]2[CH2:5][N:4]1[NH:3][C:12]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=12

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 218852-DimethylaminopyridineHCID 86614230HCID 86614230, compound

Product 1

HCID 59701085HCID 59701085, compoundYield 80.8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

5.63 g of the product obtained in stage D are dissolved in 2 l of acetonitrile. 8.45 g of triethylamine are slowly added, followed, at 0° C., by 1.658 g of diphosgene and 2.25 g of dimethylaminopyridine. The temperature is allowed to return to ambient temperature. After one hour, the acetonitrile is evaporated and the residue is treated with NaH2PO4 (1M aqueous solution). Extraction is carried out with AcOEt, and the organic phase is washed with water. It is dried over MgSO4 and the solvent is evaporated. The residue is chromatographed on silica (eluent: heptane/AcOEt (4:1)). The compound obtained is crystallized from ether at 0° C. and 1.96 g of the expected product (41%) are isolated.

Workup

  1. customto return to ambient temperature
  2. customthe acetonitrile is evaporated
  3. additionthe residue is treated with NaH2PO4 (1M aqueous solution)
  4. extractionExtraction
  5. washthe organic phase is washed with water
  6. dry with materialIt is dried over MgSO4
  7. customthe solvent is evaporated
  8. customThe residue is chromatographed on silica (eluent: heptane/AcOEt (4:1))
  9. customThe compound obtained
  10. customis crystallized from ether at 0° C.

Sources & evidence

ORD record
ord-b32b11c066b94935b3e8aec2c9c88893
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

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