Sulfuric Acid → 4-nitro-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-ylamine

HRID 1360835

Reaction equation

HRID 1360835 reaction equation
[N+:1]([O-:4])([O-])=[O:2].[Na+].[S:6]1[C:10]2[C:11]3[CH:17]=[N:16][NH:15][C:12]=3[CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[NH2:18].S(=O)(=O)(O)O>>[N+:1]([C:14]1[C:9]2[N:8]=[C:7]([NH2:18])[S:6][C:10]=2[C:11]2[CH:17]=[N:16][NH:15][C:12]=2[CH:13]=1)([O-:4])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric AcidHCID 24268Sodium NitrateHCID 450776746H-thiazolo[5,4-e]indazol-2-amine

Product 1

HCID 579512644-nitro-6H-pyrazolo[4',3':3,4]benzo[1,2-d]thiazol-2-ylamineYield 68%

Procedure

Under ice-cooling, 184 mg (2.17 mmol) of sodium nitrate was added to a mixture of 191 mg (1.01 mmol) of 6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-ylamine and 3 ml of concentrated sulfuric acid, and the mixture was stirred for 0.5 hours. The reaction mixture was poured onto ice, and the precipitated solid was collected by filtration, and then washed with water and methanol to give 160 mg (yield: 68%) of 4-nitro-6H-pyrazolo[4′,3′:3,4]benzo[1,2-d]thiazol-2-ylamine.

Workup

  1. temperatureUnder ice-cooling
  2. additionThe reaction mixture was poured onto ice
  3. filtrationthe precipitated solid was collected by filtration
  4. washwashed with water and methanol

Sources & evidence

ORD record
ord-0bed401fe72d48eebf2cae23634b86ec
Source dataset
uspto-grants-2011_02
Patent number
US07879887B2

Linked notes

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