Dichloromethane → N-(4-methoxybenzyl)-1H-imidazole-1-carboxamide

HRID 1589788Notes

Reaction equation

HRID 1589788 reaction equation
[C:1]([N:8]1[CH:12]=[CH:11]N=C1)([N:3]1[CH:7]=[CH:6][N:5]=[CH:4]1)=[O:2].[CH3:13][O:14][C:15]1[CH:22]=[CH:21]C(CN)=[CH:17][CH:16]=1.C(Cl)Cl>O1CCCC1>[CH3:13][O:14][C:15]1[CH:22]=[CH:21][C:11]([CH2:12][NH:8][C:1]([N:3]2[CH:7]=[CH:6][N:5]=[CH:4]2)=[O:2])=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 6344DichloromethaneHCID 682631,1'-CarbonyldiimidazoleHCID 754524-Methoxybenzylamine

Product 1

HCID 9991495N-(4-methoxybenzyl)-1H-imidazole-1-carboxamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

23.6 g of carbonyldiimidazole are added in portions to a solution of 20 g of 4-methoxybenzylamine in 100 ml of anhydrous tetrahydrofuran, the temperature being kept below 10° C. When the addition is complete, the mixture is allowed to return to room temperature and stirring is maintained for three hours. After filtration, the tetrahydrofuran phase is evaporated under vacuum and the residue obtained is taken up with methylene chloride, washed with water and then dried. The oil obtained after evaporation of the methylene chloride is crystallized from ether. The crystals obtained are filtered off and then dried. 22.7 g of N-(4-methoxybenzyl)imidazolecarboxamide are thus recovered in the form of crystals melting at 117° C.

Workup

  1. custombeing kept below 10° C
  2. additionWhen the addition
  3. customto return to room temperature
  4. temperatureis maintained for three hours
  5. filtrationAfter filtration
  6. customthe tetrahydrofuran phase is evaporated under vacuum
  7. customthe residue obtained
  8. washwashed with water
  9. customdried
  10. customThe oil obtained
  11. customafter evaporation of the methylene chloride
  12. customis crystallized from ether
  13. customThe crystals obtained
  14. filtrationare filtered off
  15. customdried
  16. custom22.7 g of N-(4-methoxybenzyl)imidazolecarboxamide are thus recovered in the form of crystals melting at 117° C.

Sources & evidence

ORD record
ord-e9904591839841c786e9ef790ee46afc
Source dataset
uspto-grants-1993_04
Patent number
US05200408

Reaction notes

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