Hydrochloric Acid → HCID 178489241, compound

HRID 1165588Notes

Reaction equation

HRID 1165588 reaction equation
[C:1](N1C=CN=C1)(N1C=CN=C1)=[O:2].CO[C:15]1[CH:16]=[CH:17][C:18]2[C:22]([O:23][CH:24]([CH3:26])[CH3:25])=[C:21]([C:27]([OH:29])=O)[S:20][C:19]=2[CH:30]=1.[NH2:31][C:32]1[NH:36][N:35]=[N:34][N:33]=1.Cl>O1CCCC1.O>[CH3:1][O:2][C:17]1[C:18]2[C:22]([O:23][CH:24]([CH3:25])[CH3:26])=[C:21]([C:27]([NH:31][C:32]3[NH:36][N:35]=[N:34][N:33]=3)=[O:29])[S:20][C:19]=2[CH:30]=[CH:15][CH:16]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 682631,1'-CarbonyldiimidazoleHCID 13961646HCID 13961646, compoundHCID 178509299HCID 178509299, compound

Product 1

HCID 178489241HCID 178489241, compoundYield 60%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Carbonyldiimidazole (3.8 g, 23 mmoles) is added to a stirred solution of 6-methoxy-3-(1-methylethoxy)benzo[b]thiophene-2-carboxylic acid (5.4 gg, 20 mmoles) in tetrahydrofuran (75 mls) under nitrogen, and the mixture is heated under reflux. After 75 minutes 5-aminotetrazole (1.66 g. 20 mmoles) is added. After an additional three hours under reflux the mixture is stirred into water (350 mls) and acidified with concentrated HCl. The resulting precipitate is filtered off, rinsed with water, and dried. Recrystallization from DMF/methanol gave the pure product (4.0 g): mp=233°-234? C. (dec).

Workup

  1. temperaturethe mixture is heated
  2. temperatureunder reflux
  3. temperatureAfter an additional three hours under reflux the mixture
  4. filtrationThe resulting precipitate is filtered off
  5. washrinsed with water
  6. customdried
  7. customRecrystallization from DMF/methanol

Sources & evidence

ORD record
ord-d0000079b0ee497487e6753ce6ee4b6d
Source dataset
uspto-grants-1990_03
Patent number
US04910317

Reaction notes

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