Dimethylformamide → HCID 178475082, compound

HRID 1106121Notes

Reaction equation

HRID 1106121 reaction equation
[C:1]([NH:4][C@@H:5]([C:9]([NH:11][C:12]1[CH:17]=[CH:16][C:15]([C:18]2[N:23]=[C:22]([OH:24])[C:21]([C:25]([OH:27])=[O:26])=[CH:20][N:19]=2)=[CH:14][CH:13]=1)=[O:10])[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2].C(N1C=CN=C1)(N1C=CN=C1)=O.CN(C)C=O.O1CCCC1>CCOCC>[N-:23]1[CH:22]=[CH:21][N:19]=[CH:18]1.[C:1]([NH:4][C@@H:5]([C:9]([NH:11][C:12]1[CH:13]=[CH:14][C:15]([C:18]2[N:23]=[C:22]([OH:24])[C:21]([C:25]([OH:27])=[O:26])=[CH:20][N:19]=2)=[CH:16][CH:17]=1)=[O:10])[CH:6]([CH3:8])[CH3:7])(=[O:3])[CH3:2]

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 178475081HCID 178475081, compound

Product 1

HCID 178475082HCID 178475082, compoundYield 119.7%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Procedure

A mixture of 3.72 g (10 mmol) of the above pyrimidine acid, 3.24 g (20 mmol) of carbonyldiimidazole, and 25 ml of dimethylformamide is stirred at 49°-52° C. for 30 min. The solution is treated with 50 ml of tetrahydrofuran and 200 ml of ether and stored in the cold overnight. The solid is filtered, washed with ether and dried to give 2.63 g of the title imidazolide.

Workup

  1. customstored in the cold overnight
  2. filtrationThe solid is filtered
  3. washwashed with ether
  4. customdried

Sources & evidence

ORD record
ord-d903c78d1c674dc4ab52fe6ef1beb73c
Source dataset
uspto-grants-1982_01
Patent number
US04311699

Reaction notes

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