Hydrochloric Acid → HCID 178420499, compound

HRID 1361011Notes

Reaction equation

HRID 1361011 reaction equation
[N-:1]=[N+:2]=[N-:3].[Na+].[Cl-].[NH4+].[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][CH2:18][C:19]1[CH:20]=[C:21]([CH:24]=[CH:25][CH:26]=1)[C:22]#[N:23].Cl>CN(C)C=O>[CH:7]1[C:16]2[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=2)[CH:10]=[CH:9][C:8]=1[O:17][CH2:18][C:19]1[CH:20]=[C:21]([C:22]2[NH:23][N:3]=[N:2][N:1]=2)[CH:24]=[CH:25][CH:26]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 12222182HCID 12222182, compound

Product 1

HCID 178420499HCID 178420499, compoundYield 93%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

To a mixture of sodium azide (1.46 g, 22.5 mmol) and ammonium chloride (1.28 g, 24.0 mmol) in dry dimethylformamide (20 mL) under an atmosphere of nitrogen, 3-(naphthalen-2-yloxymethyl)-benzonitrile (3.9 g, 15 mmol) was added and the reaction mixture was stirred at 125° C. for 4 hours. The cooled reaction mixture was poured on to ice water (300 mL) and acidified to pH=1 with 1 N hydrochloric acid. The precipitate was filtered off and washed with water, dried at 100° C. for 4 hours affording 4.2 g (93%) of the title compound.

Workup

  1. customThe cooled reaction mixture
  2. filtrationThe precipitate was filtered off
  3. washwashed with water
  4. customdried at 100° C. for 4 hours

Sources & evidence

ORD record
ord-eedc975c4f96461793cc6cd1b866757d
Source dataset
uspto-grants-2011_02
Patent number
US07879893B2

Reaction notes

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