Dimethylformamide → HCID 19040023, compound

HRID 1684639Notes

Reaction equation

HRID 1684639 reaction equation
[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH:19]=O)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([N:30]1C=C[N:32]=[CH:31]1)([N:25]1C=CN=C1)=[O:24].C(N(CC)CC)C.CN(C=[O:46])C>O>[C:1]1([C:7]2[O:8][CH:9]=[C:10]([CH2:12][CH2:13][O:14][C:15]3[CH:22]=[CH:21][C:18]([CH2:19][N:32]4[C:31](=[O:46])[NH:30][C:23](=[O:24])[NH:25]4)=[CH:17][CH:16]=3)[N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8471TriethylamineHCID 682631,1'-CarbonyldiimidazoleHCID 10685112HCID 10685112, compound

Product 1

HCID 19040023HCID 19040023, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
25 °C

Procedure

A mixture of 11.9 g of semicarbazide from Example 17 Part C, 8.10 g of carbonyldiimidazole, 0.5 mL of triethylamine and 400 mL of anhydrous DMF was stirred at 25° C. for 4 days, diluted with 1 L of H2O and filtered. The filtrate was evaporated. The residue was treated with 100 mL of MeOH and the solid was filtered and dried to give 3.43 g of 1-[(4-(2-(2-phenyl-4-oxazolyl)ethoxy)phenyl)methyl]1,2,4-triazolidin-3,5-dione (27%. mp 223.5°-230° C.).

Workup

  1. filtrationfiltered
  2. customThe filtrate was evaporated
  3. additionThe residue was treated with 100 mL of MeOH
  4. filtrationthe solid was filtered
  5. customdried

Sources & evidence

ORD record
ord-f3ed5f6705ab487e8499cca500e83f2a
Source dataset
uspto-grants-1997_06
Patent number
US05641796

Reaction notes

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