Hydrochloric Acid → HCID 178458114, compound

HRID 621807Notes

Reaction equation

HRID 621807 reaction equation
[Br:1][C:2]1[C:3]([O:17][CH:18]([CH3:20])[CH3:19])=[C:4]([C:14](O)=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:33][C:34]1[NH:38][N:37]=[N:36][N:35]=1.Cl>C1COCC1>[Br:1][C:2]1[C:3]([O:17][CH:18]([CH3:20])[CH3:19])=[C:4]([C:14]([NH:33][C:34]2[NH:38][N:37]=[N:36][N:35]=2)=[O:15])[N:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[C:6]=1[Br:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14154274HCID 14154274, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178458114HCID 178458114, compoundYield 34%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 4,5-dibromo-3-(1-methylethoxy)-1-phenyl-1H-pyrrole-2-carboxylic acid (2.0 g, 0.005 moles) and 1,1'-carbonyldiimidazole (0.8 g, 0.005 moles) in THF (25 mL) is heated under argon to reflux. After 1 hour, 5-aminotetrazole (0.4 g, 0.005 moles) is added. After 2.5 hours, the mixture is stirred into ice water (250 mL) and acidified with dilute HCl. The precipitate is filtered off, rinsed with water and dried. Recrystallization from methyl t-butyl ether gave the pure product (0.8 g); mp 184° C. (dec).

Workup

  1. temperatureto reflux
  2. waitAfter 2.5 hours
  3. filtrationThe precipitate is filtered off
  4. washrinsed with water
  5. customdried
  6. customRecrystallization from methyl t-butyl ether

Sources & evidence

ORD record
ord-573b771240ce42ff850b33822af43692
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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