Hydrochloric Acid → HCID 178435068, compound

HRID 621825Notes

Reaction equation

HRID 621825 reaction equation
[Br:1][C:2]1[C:3]([S:11][CH:12]([CH3:14])[CH3:13])=[C:4]([C:8](O)=[O:9])[S:5][C:6]=1[CH3:7].C(N1C=CN=C1)(N1C=CN=C1)=O.[NH2:27][C:28]1[NH:32][N:31]=[N:30][N:29]=1.Cl>C1COCC1>[Br:1][C:2]1[C:3]([S:11][CH:12]([CH3:14])[CH3:13])=[C:4]([C:8]([NH:27][C:28]2[NH:32][N:31]=[N:30][N:29]=2)=[O:9])[S:5][C:6]=1[CH3:7]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 14154194HCID 14154194, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178435068HCID 178435068, compoundYield 96.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 4-bromo-5-methyl-3-[(1-methylethyl) thio]-2-thiophenecarboxylic acid (3.0 g, 10 mmoles) and 1,1'-carbonyldiimidazole (1.8 g, 11 mmoles) in THF (25 mL) is stirred under argon and heated under reflux. After 1.5 hours 5-aminotetrazole (0.87 g, 10 mmol) is added and heating continued for an additional 2.5 hours. The mixture is then cooled, stirred into ice water (300 mL) and acidified with concentrated HCl. The precipitate is filtered off, washed with 4N HCl, rinsed with water and dried to afford the product (3.5 g); mp 235° C. (dec).

Workup

  1. temperatureheated
  2. temperatureunder reflux
  3. temperatureheating
  4. temperatureThe mixture is then cooled
  5. filtrationThe precipitate is filtered off
  6. washwashed with 4N HCl
  7. washrinsed with water
  8. customdried

Sources & evidence

ORD record
ord-6b53f95ccd0a433e9d61eb4730ceccd8
Source dataset
uspto-grants-1989_04
Patent number
US04824958

Reaction notes

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