Ammonium Chloride → HCID 178477982, compound

HRID 2356743Notes

Reaction equation

HRID 2356743 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[S:9][C:10]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)=[C:11]([CH2:13][C:14]#[N:15])[N:12]=2)=[CH:4][CH:3]=1.[N-:22]=[N+:23]=[N-:24].[Na+].[Cl-].[NH4+]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[S:9][C:10]([C:16]3[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=3)=[C:11]([CH2:13][C:14]3[NH:24][N:23]=[N:22][N:15]=3)[N:12]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 67547511HCID 67547511, compound

Product 1

HCID 178477982HCID 178477982, compoundYield 66%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
90 °C

Procedure

To a solution of 2-(4-chlorophenyl)-5-phenylthiazol-4-yl acetonitrile (2.33 g) in N,N-dimethylformamide (30 ml) were added sodium azide (1.40 g) and ammonium chloride (1.3 g), and the mixture was stirred at 90° C. for 12 hours. After removing the solvent under reduced pressure, ethyl acetate and water were added to the residue. The organic layer was collected, dried and the solvent was removed under reduced pressure. The residue was recrystallized from chloroform and methanol to obtain 5-[2-(4-chlorophenyl)-5-phenyl-thiazol-4-ylmethyl]tetrazole (1.75 g).

Workup

  1. customAfter removing the solvent under reduced pressure, ethyl acetate and water
  2. additionwere added to the residue
  3. customThe organic layer was collected
  4. customdried
  5. customthe solvent was removed under reduced pressure
  6. customThe residue was recrystallized from chloroform and methanol

Sources & evidence

ORD record
ord-e280e262120d456c8d617e955bef1c71
Source dataset
uspto-grants-2010_07
Patent number
US07759373B2

Reaction notes

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