Ammonia → HCID 59402727, compound

HRID 538539Notes

Reaction equation

HRID 538539 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][N:19]=3)[C:15]#[N:16])=[N:7][C:6]=2[CH:20]=1.[OH2:21].N>OS(O)(=O)=O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[S:9][C:8]([CH2:10][O:11][C:12]3[CH:13]=[C:14]([CH:17]=[CH:18][N:19]=3)[C:15]([NH2:16])=[O:21])=[N:7][C:6]=2[CH:20]=1

Participants

5

Reactant 3

HCID 222AmmoniaHCID 962WaterHCID 59402661HCID 59402661, compound

Product 1

HCID 59402727HCID 59402727, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Conditions

Temperature
40 °C

Procedure

2-[(5-Chloro-1,3-benzothiazol-2-yl)methoxy]isonicotinonitrile (40 mg, 0.13 mmol) was dissolved in conc. H2SO4 (0.36 ml) and the solution was heated at 40° C., under vigorous stirring. Water (50 mg) was added dropwise and the mixture was stirred at 40° C. for 3 h. After cooling at −5° C., crushed ice (25 ml) was added quickly, with vigorous stirring, and the mixture was stirred at r.t. for two more hours. Ammonia solution was added (pH 10) and the precipitant solid was filtered, rinsed with H2O and dried. The brown solid was purified by preparative TLC, eluted with EtOAc, to give 20 mg (47% yield), mp 220-222° C., HPLC-MS (method 1): m/z 320 [M+H]+, Rt=3.76 min.

Workup

  1. temperatureAfter cooling at −5° C.
  2. additionwas added quickly, with vigorous stirring
  3. stirringthe mixture was stirred at r.t. for two more hours
  4. filtrationthe precipitant solid was filtered
  5. washrinsed with H2O
  6. customdried
  7. customThe brown solid was purified by preparative TLC
  8. washeluted with EtOAc
  9. customto give 20 mg (47% yield), mp 220-222° C., HPLC-MS (method 1)

Sources & evidence

ORD record
ord-36845f470bc94b7ea0189a733821de1e
Source dataset
uspto-grants-2014_10
Patent number
US08865736B2

Reaction notes

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