Water → HCID 19385238, compound

HRID 1468674Notes

Reaction equation

HRID 1468674 reaction equation
[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][C:6]2[N:7]=[C:8](N)[S:9][C:5]=2[CH:4]=1.N([O-])=O.[Na+].O.C([O-])([O-])=O.[Na+].[Na+]>OP(O)(O)=O>[CH3:1][O:2][C:3]1[C:12]([CH3:13])=[CH:11][C:6]2[N:7]=[CH:8][S:9][C:5]=2[CH:4]=1

Participants

6

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 20289145HCID 20289145, compoundHCID 23668193Sodium Nitrite

Product 1

HCID 19385238HCID 19385238, compound

Reagents, catalysts & solvents 1

HCID 1004Phosphoric AcidSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-methoxy-5-methylbenzo[d]thiazol-2-amine (5A) (1.24 g, 6.42 mmol) in H3PO4 (5 mL) at 0° C., was added NaNO2 (2.2 g, 32 mmol) in minimal amount of water. The reaction mixture was stirred at 0° C. for 20 min. The reaction mixture was then transferred to ice-cold hypophosphorous acid (50%, 5 ml) and slowly warmed to room temperature and stirred at room temperature until gas evolution ceases. Solid Na2CO3 was added to neutralize the reaction and the mixture was extracted by ethyl acetate. The organic phase was dried over MgSO4, filtered, concentrated and purified by silica gel column (0-100% ethyl acetate/hexanes). LCMS-ESI+: calc'd for C9H9NOS: 180.0 (M+H+). Found: 180.1 (M+H+).

Workup

  1. temperatureslowly warmed to room temperature
  2. stirringstirred at room temperature until gas evolution ceases
  3. customthe reaction
  4. extractionthe mixture was extracted by ethyl acetate
  5. dry with materialThe organic phase was dried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated
  8. custompurified by silica gel column (0-100% ethyl acetate/hexanes)

Sources & evidence

ORD record
ord-a5f707168ffb46e9bf1a90de3d9cfc5e
Source dataset
uspto-grants-2015_04
Patent number
US09006229B2

Reaction notes

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