Hydrochloric Acid → HCID 178522682, compound

HRID 614816Notes

Reaction equation

HRID 614816 reaction equation
[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11](O)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:19][C:20]1[NH:24][N:23]=[N:22][N:21]=1.[Si](Cl)(Cl)(Cl)Cl.Cl>O.N1C=CC=CC=1>[CH2:1]([O:8][C:9]1[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][C:10]=1[C:11]([NH:19][C:20]1[NH:24][N:23]=[N:22][N:21]=1)=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 24816Silicon tetrachlorideHCID 33011592-(benzyloxy)-5-chlorobenzoic acidHCID 178509299HCID 178509299, compound

Product 1

HCID 178522682HCID 178522682, compoundYield 20.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 1049PyridineSolvent

Conditions

Temperature
25 °C

Procedure

Dry 2-benzyloxy-5-chlorobenzoic acid (1.15 g) was treated, with stirring, with dry pyridine (20 ml) and anhydrous 5-aminotetrazole (3.72 g). The mixture was stirred at 25° C. and treated dropwise with silicon tetrachloride (0.45 g), and the mixture was then stirred at 25° C. for 20 hours. The resulting clear yellow solution was cautiously poured into a mixture of ice and water (50 ml) and the mixture was acidified to pH 1 by treatment with concentrated hydrochloric acid. The white precipitated solid was filtered off, washed with water, with ethanol and with diethyl ether, and recrystallized from a mixture of dimethylformamide and water to give 2-benzyloxy-5-chloro-N-(tetrazol-5-yl)benzamide, (0.29 g), m.p. 256°-257° C. (with decomposition).

Workup

  1. stirringthe mixture was then stirred at 25° C. for 20 hours
  2. customThe white precipitated solid
  3. filtrationwas filtered off
  4. washwashed with water, with ethanol and with diethyl ether
  5. customrecrystallized from a mixture of dimethylformamide and water

Sources & evidence

ORD record
ord-7d2b914470b94d39b06de66e120d10a2
Source dataset
uspto-grants-1979_03
Patent number
US04146631

Reaction notes

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