Hydrochloric Acid → HCID 178515108, compound

HRID 1415212Notes

Reaction equation

HRID 1415212 reaction equation
[Cl:1][C:2]1[C:18]([O:19][CH2:20][C:21]#[N:22])=[CH:17][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([CH:12]3[CH2:16][CH2:15][CH2:14][CH2:13]3)[C:10](=[O:11])[C:4]=2[C:3]=1[Cl:23].[N-:24]=[N+:25]=[N-:26].[Na+].[Cl-].[NH4+].Cl>CN(C=O)C>[Cl:1][C:2]1[C:18]([O:19][CH2:20][C:21]2[NH:26][N:25]=[N:24][N:22]=2)=[CH:17][C:5]2[CH2:6][CH2:7][CH2:8][CH:9]([CH:12]3[CH2:13][CH2:14][CH2:15][CH2:16]3)[C:10](=[O:11])[C:4]=2[C:3]=1[Cl:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 21483934HCID 21483934, compound

Product 1

HCID 178515108HCID 178515108, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of (3,4-dichloro-5-oxo-6-cyclopentyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxy)acetonitrile (5.7 g., 0.0165 mole) in DMF (25 ml.) is added sodium azide (1.26 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 gummy solid that forms is triturated with butyl chloride and then crystallized from butyl chloride-methanol to obtain 5-(3,4-dichloro-5-oxo-6-cyclopentyl-6,7,8,9-tetrahydro-5H-benzocyclohepten-2-yloxymethyl)tetrazole.

Workup

  1. temperatureThe mixture is heated at 85°-90° C. for one hour
  2. temperaturecooled
  3. customThe gummy solid that forms is triturated with butyl chloride
  4. customcrystallized from butyl chloride-methanol

Sources & evidence

ORD record
ord-d4063cdf15db4afcae24865ca1fc6a27
Source dataset
uspto-grants-1977_01
Patent number
US04003927

Reaction notes

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