Nitric Acid → HCID 178432273, compound

HRID 2289482Notes

Reaction equation

HRID 2289482 reaction equation
Cl.Cl.[NH2:3][C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([CH3:12])=[N:9][C:8]=2[CH:13]=1.C(=O)(O)[O-].[Na+].[N:19]#[C:20][NH2:21].[N+:22]([O-:25])([OH:24])=[O:23]>C(O)C.O.ClCCl>[N+:22]([O-:25])([OH:24])=[O:23].[NH:3]([C:4]1[CH:5]=[CH:6][C:7]2[S:11][C:10]([CH3:12])=[N:9][C:8]=2[CH:13]=1)[C:20]([NH2:21])=[NH:19]

Participants

8

Reactant 4

HCID 944Nitric AcidHCID 9864CyanamideHCID 516892Sodium BicarbonateHCID 162189432-Methylbenzothiazol-5-ylamine dihydrochloride

Product 1

HCID 178432273HCID 178432273, compoundYield 47.9%

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

5-Amino-2-methylbenzothiazole dihydrochloride (2.50 g, 10.54 mmol) was partitioned between dichloromethane and saturated aqueous sodium bicarbonate solution. The organic phase was dried (MgSO4) and evaporated to afford the free base which was dissolved in ethanol (5 ml). A solution of cyanamide (660 mg, 15.71 mmol) in water (1 ml) was added followed by concentrated nitric acid (69%, 0.68 ml, 10.54 mmol) and the resulting mixture was refluxed for 18 h. The solid which formed on cooling to room temperature was collected and washed with cold ethanol then diethyl ether to give the title compound (1.36 g) as a beige solid m.p. 260-261° (dec.). δH (d6DMSO) 2.80 (3H, s), 7.26 (1H, m), 7.37 (4H, s), 7.78 (1H, s), 8.08 (1H, d, J 8.6 Hz) and 9.67 (1H, br s).

Workup

  1. dry with materialThe organic phase was dried (MgSO4)
  2. customevaporated
  3. customto afford the free base which
  4. temperaturethe resulting mixture was refluxed for 18 h
  5. customThe solid which formed
  6. customwas collected
  7. washwashed with cold ethanol

Sources & evidence

ORD record
ord-0a60b41aa39f49d6b872f373f70c64b8
Source dataset
uspto-grants-2000_07
Patent number
US06093716

Reaction notes

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