Hydrochloric Acid → HCID 178431377, compound

HRID 1283875Notes

Reaction equation

HRID 1283875 reaction equation
[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([Cl:16])[C:7]([CH3:15])=[C:8]([O:11][CH2:12][C:13]#[N:14])[CH:9]=2)[C:4](=[O:17])[C:3]21[CH2:21][CH2:20][CH2:19][CH2:18]2.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+].Cl>CN(C)C=O>[O:1]=[C:2]1[C:10]2[C:5](=[C:6]([Cl:16])[C:7]([CH3:15])=[C:8]([O:11][CH2:12][C:13]3[NH:24][N:23]=[N:22][N:14]=3)[CH:9]=2)[C:4](=[O:17])[C:3]21[CH2:21][CH2:20][CH2:19][CH2:18]2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21516772HCID 21516772, compound

Product 1

HCID 178431377HCID 178431377, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
95 °C

Procedure

A stirred mixture of [1',3'-dioxo-4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-6'-yloxy]acetonitrile (9.0 g., 0.03 mole), sodium azide (3.9 g., 0.06 mole) and ammonium chloride (3.2 g., 0.06 mole) in dimethylformamide (150 ml.) is heated at 95°C. for 2 hours then cooled and poured into dilute aqueous hydrochloric acid affording 9.9 g. of 5-[1',3'-dioxo-4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-6'-yloxymethyl]tetrazole which melts at 211°-212°C. after recrystallization from acetic acid-water.

Workup

  1. temperaturethen cooled
  2. customof 5-[1',3'-dioxo-4'-chloro-5'-methylspiro(cyclopentane-1,2'-indan)-6'-yloxymethyl]tetrazole which melts at 211°-212°C. after recrystallization from acetic acid-water

Sources & evidence

ORD record
ord-02751443c9ec4aaeaa5f170ac6faf571
Source dataset
uspto-grants-1976_08
Patent number
US03976681

Reaction notes

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