Thionyl Chloride → HCID 178486594, compound

HRID 1388675Notes

Reaction equation

HRID 1388675 reaction equation
[CH3:1][O:2][C:3]1[C:4]([C:13]([OH:15])=O)=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2.[NH2:16][C:17]1[NH:21][N:20]=[N:19][N:18]=1.S(Cl)(Cl)=O>N1C=CC=CC=1>[CH3:1][O:2][C:3]1[C:4]([C:13]([NH:16][C:17]2[NH:21][N:20]=[N:19][N:18]=2)=[O:15])=[CH:5][C:6]2[C:11]([CH:12]=1)=[CH:10][CH:9]=[CH:8][CH:7]=2

Participants

5

Reactant 3

HCID 24386Thionyl ChlorideHCID 701613-Methoxy-2-naphthoic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178486594HCID 178486594, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

To a mixture of 8.2 g. of 3-methoxy-2-naphthoic acid, 5.2 g. of aminotetrazole, and 80 ml. of pyridine was added dropwise 6.4 ml. of thionyl chloride, maintaining the temperature below 70° C. After stirring for one hour, the mixture was cooled to 25° C. and evaporated to dryness. The residue was washed with dilute hydrochloric acid, then recrystallized from N,N-dimethylformamide, then dissolved in base, filtered, reprecipitated with dilute acid, filtered, washed with methanol, then recrystallized again from N,N-dimethylformamide to provide 3-methoxy-N-(tetrazol-5-yl)naphthalene-2-carboxamide (a type IV compound), m.p. 280°-283° C.

Workup

  1. additionTo a mixture of 8.2 g
  2. customevaporated to dryness
  3. washThe residue was washed with dilute hydrochloric acid
  4. customrecrystallized from N,N-dimethylformamide
  5. dissolutiondissolved in base
  6. filtrationfiltered
  7. customreprecipitated
  8. additionwith dilute acid
  9. filtrationfiltered
  10. washwashed with methanol
  11. customrecrystallized again from N,N-dimethylformamide

Sources & evidence

ORD record
ord-cdc1de1a1b6f4cafadf85ba5fafa7550
Source dataset
uspto-grants-1984_02
Patent number
US04432986

Reaction notes

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