4-Iodobenzoic acid → HCID 13588882, compound

HRID 1589167Notes

Reaction equation

HRID 1589167 reaction equation
[I:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][CH:3]=1.C(N1C=CN=C1)(N1C=CN=C1)=O.[N:23]1([CH2:28][CH2:29][CH2:30][NH2:31])[CH:27]=[N:26][CH:25]=[N:24]1>O>[I:1][C:2]1[CH:3]=[CH:4][C:5]([C:6]([NH:31][CH2:30][CH2:29][CH2:28][N:23]2[CH:27]=[N:26][CH:25]=[N:24]2)=[O:8])=[CH:9][CH:10]=1

Participants

5

Reactant 3

HCID 120854-Iodobenzoic acidHCID 682631,1'-CarbonyldiimidazoleHCID 43796821H-1,2,4-Triazole-1-propanamine

Product 1

HCID 13588882HCID 13588882, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of about 2.48 g of 4-iodobenzoic acid, about 1.62 g of 1,1'-carbonyldiimidazole and about 30 ml oftetrahydrofuran was stirred for about 3 hours, then about 1.3 ml of 1H-1,2,4-triazole-1-propanamine was added and stirring was continued overnight. The mixture was heated for about 2 hours, about 5 ml of water was added, heating was continued for an additional hour then the mixture was concentrated to a residue. Methylene chloride and about 10 ml of approximately 1N sodium hydroxide were added. The organic layer was separated, washed with water, dried and concentrated, giving about 2.7 g of the desired product as a white solid, mp 132°-134° C.

Workup

  1. stirringstirring
  2. waitwas continued overnight
  3. temperatureThe mixture was heated for about 2 hours
  4. temperatureheating
  5. waitwas continued for an additional hour
  6. concentrationthe mixture was concentrated to a residue
  7. additionMethylene chloride and about 10 ml of approximately 1N sodium hydroxide were added
  8. customThe organic layer was separated
  9. washwashed with water
  10. customdried
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-43783271b4f843e683283aa948e7d9db
Source dataset
uspto-grants-1986_02
Patent number
US04568685

Reaction notes

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