Ammonium Chloride → N-(benzo[d]thiazole-2-yl)-2-(2H-tetrazole-5-yl)acetamide

HRID 1472143Notes

Reaction equation

HRID 1472143 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:15])[CH2:12][C:13]#[N:14].[NH4+].[Cl-].[N-:18]=[N+:19]=[N-:20].[Na+]>CN(C)C=O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[NH:10][C:11](=[O:15])[CH2:12][C:13]1[N:18]=[N:19][NH:20][N:14]=1

Participants

5

Reactant 3

HCID 25517Ammonium ChlorideHCID 33557Sodium AzideHCID 4530340N-(1,3-benzothiazol-2-yl)-2-cyanoacetamide

Product 1

HCID 86660694N-(benzo[d]thiazole-2-yl)-2-(2H-tetrazole-5-yl)acetamideYield 20%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
120 °C

Procedure

N-(benzo[d]thiazole-2-yl)-2-cyanoacetamide (0.1 g), NH4Cl (5.0 eq, 0.1 g), and NaN3 (5.2 eq, 0.13 g) were dissolved on 2.1 mL of DMF (dimethylformamide), and heated at 120° C. for 6 hours. DMF was removed under reduced pressure distillation, and 10 ml of water and 5% NaOH solution were added thereto. The aqueous layer was washed with 15 ml of Et2O, and treated with activated carbon. To the obtained reaction mixture, 10% aqueous hydrochloric acid, making the solution with pH 2. The obtained reaction mixture was extracted with methylene chloride, to produce N-(benzo[d]thiazole-2-yl)-2-(2H-tetrazole-5-yl)acetamide (20%, 21 mg) in light yellow solid phase.

Workup

  1. customDMF was removed under reduced pressure distillation, and 10 ml of water and 5% NaOH solution
  2. additionwere added
  3. washThe aqueous layer was washed with 15 ml of Et2O
  4. additiontreated with activated carbon
  5. customTo the obtained reaction mixture, 10% aqueous hydrochloric acid
  6. customThe obtained reaction mixture
  7. extractionwas extracted with methylene chloride

Sources & evidence

ORD record
ord-5ebc77ace50a49899e646e4287a3be39
Source dataset
uspto-grants-2015_04
Patent number
US09012481B2

Reaction notes

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