Hydrochloric Acid → Benzo[d]thiazole-2-carbonyl azide

HRID 409747Notes

Reaction equation

HRID 409747 reaction equation
[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([NH:12][NH2:13])=[O:11].Cl.[N:15]([O-])=O.[Na+]>O>[S:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([N:12]=[N+:13]=[N-:15])=[O:11]

Participants

5

Reactant 3

HCID 313Hydrochloric AcidHCID 3514191,3-Benzothiazole-2-carbohydrazideHCID 23668193Sodium Nitrite

Product 1

HCID 57947425Benzo[d]thiazole-2-carbonyl azideYield 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
2.5 °C

Procedure

To a suspension of benzo[d]thiazole-2-carbohydrazide (9.3 g, 48.2 mmol) in aqueous HCl (1 N, 75 mL, 75 mmol) and water (200 mL) was added a solution of NaNO2 (6.9 g, 100 mmol) in water (50 mL) dropwise at 0-5° C. The mixture was stirred at 0-5° C. for 2 h and RT for 2 h. The precipitate was filtered, washed with cold water, and dried under high vacuum to give benzo[d]thiazole-2-carbonyl azide (9.0 g, 92%). LRMS (M+H+) m/z 205.1.

Workup

  1. filtrationThe precipitate was filtered
  2. washwashed with cold water
  3. customdried under high vacuum

Sources & evidence

ORD record
ord-b4a77d6564754d7f93491aa3e6a34141
Source dataset
uspto-grants-2014_06
Patent number
US08759374B2

Reaction notes

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