Triethylamine → HCID 59701086, compound

HRID 902048Notes

Reaction equation

HRID 902048 reaction equation
Cl.Cl.[C:3]1([CH2:9][O:10][NH:11][CH:12]2[C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[NH:15][NH:14][CH2:13]2)[CH:8]=[CH:7][CH:6]=[CH:5][CH: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>[C:3]1([CH2:9][O:10][N:11]2[CH:12]3[CH2:13][N:14]([NH:15][C:16]4[CH:17]=[CH:18][CH:19]=[CH:20][C:21]=43)[C:30]2=[O:29])[CH:4]=[CH:5][CH:6]=[CH:7][CH:8]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 10426DiphosgeneHCID 218852-DimethylaminopyridineHCID 86614228HCID 86614228, compound

Product 1

HCID 59701086HCID 59701086, compoundYield 135.7%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3.13 g of the compound obtained in stage C are dissolved in 1.9 l of acetonitrile. 4.81 g (6.6 ml) of triethylamine are added dropwise over 10 minutes. 0.943 g (575 μl) of diphosgene is subsequently added slowly at 0° C., followed by 1.27 g of dimethylaminopyridine. The temperature is subsequently 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 a heptane/AcOEt 1:2 mixture and washing is carried out with water. The organic phase is dried over MgSO4 and evaporated to dryness. This residue is crystallized from ether at 0° C. 1.82 g of the expected compound (68%) are obtained.

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. washwashing
  6. dry with materialThe organic phase is dried over MgSO4
  7. customevaporated to dryness
  8. customThis residue is crystallized from ether at 0° C

Sources & evidence

ORD record
ord-7d15ab8ef1c24f6f98ec5f401764db98
Source dataset
uspto-grants-2008_04
Patent number
US07365071B2

Reaction notes

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