Hydrochloric Acid → HCID 178420784, compound

HRID 322389Notes

Reaction equation

HRID 322389 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([C:9]2[O:10][CH:11]=[C:12]([CH2:14][O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][CH2:24][N:25]4[CH:29]=[CH:28][N:27]=[CH:26]4)=[CH:18][CH:17]=3)[N:13]=2)=[CH:5][CH:4]=1)#[N:2].[N-:30]=[N+:31]=[N-:32].[Na+].[Cl-].[NH4+].Cl>O.CN(C)C=O>[N:25]1([CH2:24][CH2:23][CH2:22][C:19]2[CH:20]=[CH:21][C:16]([O:15][CH2:14][C:12]3[N:13]=[C:9]([C:6]4[CH:7]=[CH:8][C:3]([C:1]5[NH:32][N:31]=[N:30][N:2]=5)=[CH:4][CH:5]=4)[O:10][CH:11]=3)=[CH:17][CH:18]=2)[CH:29]=[CH:28][N:27]=[CH:26]1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 220097612-(4-Cyanophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole

Product 1

HCID 178420784HCID 178420784, compoundYield 33%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A mixture of 2-(4-cyanophenyl)-4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]oxazole (700 mg), sodium azide (585 mg), ammonium chloride (480 mg) and N,N-dimethylformamide (20 ml) was stirred for 24 hours at temperatures ranging from 130 to 135° C. The reaction mixture was poured into water, which was neutralized with 1N hydrochloric acid. The resulting crystalline precipitate was collected by filtration. The filtrate was subjected to extraction with ethyl acetate-tetrahydrofuran. The organic layer was washed with water, dried (MgSO4), and concentrated to leave a crystalline product. Both crystalline products were combined and recrystallized from methanol to give 5-[4-[4-[4-[3-(1-imidazolyl)propyl]phenoxymethyl]-2-oxazolyl]phenyl]-1H-tetrazole (250 mg, 33%) as colorless prisms, mp 273-275° C. (decomp.).

Workup

  1. customranging from 130 to 135° C
  2. filtrationThe resulting crystalline precipitate was collected by filtration
  3. extractionThe filtrate was subjected to extraction with ethyl acetate-tetrahydrofuran
  4. washThe organic layer was washed with water
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated
  7. customto leave a crystalline product
  8. customrecrystallized from methanol

Sources & evidence

ORD record
ord-a8fa589adeed49dcb45a2efb2f9899f4
Source dataset
uspto-grants-2001_04
Patent number
US06211215B1

Reaction notes

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