Hydrochloric Acid → HCID 178515107, compound

HRID 1415207Notes

Reaction equation

HRID 1415207 reaction equation
[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([Cl:21])[C:10]([Cl:20])=[C:11]([O:16][CH2:17][C:18]#[N:19])[CH:12]=3)[C:7]2=[O:22])[CH2:5][CH2:4][CH2:3][CH2:2]1.[N-:23]=[N+:24]=[N-:25].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[CH:1]1([CH:6]2[CH2:15][CH2:14][C:13]3[C:8](=[C:9]([Cl:21])[C:10]([Cl:20])=[C:11]([O:16][CH2:17][C:18]4[NH:25][N:24]=[N:23][N:19]=4)[CH:12]=3)[C:7]2=[O:22])[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21483905HCID 21483905, compound

Product 1

HCID 178515107HCID 178515107, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 2-cyclopentyl-6-cyanomethoxy-7,8-dichloro-1- tetralone (5.6 g., 0.0165 mole) in DMF (25 ml.) is added sodium azide (12.6 g., 0.0194 mole) and ammonium chloride (1.05 g., 0.0194 mole). The mixture is heated at 85°-90° C. for one hour, cooled and poured into ice water. The mixture is acidified with 6 N HCl. The dark gummy solid that forms is triturated with butyl chloride to obtain a solid, which is crystallized from a mixture of butyl chloride and methanol to obtain 2-cyclopentyl-6-(5-tetrazolylmethoxy)- 7,8-dichloro-1-tetralone.

Workup

  1. temperatureThe mixture is heated at 85°-90° C. for one hour
  2. temperaturecooled
  3. customThe dark gummy solid that forms is triturated with butyl chloride
  4. customto obtain a solid, which
  5. customis crystallized from a mixture of butyl chloride and methanol

Sources & evidence

ORD record
ord-fb900002a39c4e79bb3e2b3c7b384fc0
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

Loading…