Hydrochloric Acid → HCID 15541432, compound

HRID 2300397Notes

Reaction equation

HRID 2300397 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1.[C:11](Cl)(Cl)=[S:12].Cl.[CH2:16]([N:18](CC)[CH2:19]C)C>C(Cl)(Cl)Cl.C([O-])(O)=O.[Na+].C1COCC1.ClCCN>[S:12]1[CH2:11][CH2:19][N:18]=[C:16]1[NH:1][C:2]1[CH:10]=[CH:9][C:5]2[N:6]=[CH:7][S:8][C:4]=2[CH:3]=1

Participants

9

Reactant 4

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 10040ThiophosgeneHCID 682886-Aminobenzothiazole

Product 1

HCID 15541432HCID 15541432, compoundYield 68%

Reagents, catalysts & solvents 4

HCID 6212ChloroformSolventHCID 8028TetrahydrofuranSolventHCID 133692-ChloroethylamineSolventHCID 516892Sodium BicarbonateSolvent

Conditions

Temperature
25 °C

Procedure

To a solution of 6-aminobenzothiazole (0.15 g, 1.0 mmol) in 10 mL of CHCl3 and 10 mL of saturated aqueous NaHCO3 was added thiophosgene (0.20 mL, 2.6 mmol) in a portion. The reaction mixture was stirred for 1 h at 25° C. organic layer was separated from aqueous layer. Aqueous layer was then extracted with EtOAc several times. Combined organic extracts were dried over Na2SO4 and concentrated in vacuo t providing an oil which was dissolved in 10 mL of THF with of triethylamine (1 mL) and chloroethylamine.HCl (0.5 H). Resulting solution was stirred for 12 h at reflux. It was concentrated in vacuo to yield oily residue which was purified on column chromatography (5%. NH3 saturated MeOH/EtOAc) to provide 0.16 g (0.68 mmol, 68%) of the desired product. The product obtained was converted to the fumarate salt and recrystallized from MeOH to provide 0.18 g of the product as a white crystal: mp 181-183° C.; 1H NMR (CD3OD) δ 9.11 (s, 1H), 8.02 (d, J=2.0 Hz, 1H), 7.96 (d, J=5.8 Hz, 1H), 7.32 (dd, J=2.0, 5.8 Hz, 1H), 3.90 (t, J=4.8 Hz, 2H), 3.39 (t, J=4.8 Hz, 2H); Anal. Calc. for C10H9N3S2.1.0C4H4O4 requires C, 47.85; H, 3.73; N, 11.96. Found: C, 48.86; H. 3.86; N, 12.15.

Workup

  1. customwas separated from aqueous layer
  2. extractionAqueous layer was then extracted with EtOAc several times
  3. dry with materialCombined organic extracts were dried over Na2SO4
  4. concentrationconcentrated in vacuo t
  5. customproviding an oil which
  6. stirringResulting solution was stirred for 12 h
  7. temperatureat reflux
  8. concentrationIt was concentrated in vacuo
  9. customto yield oily residue which
  10. customwas purified on column chromatography (5%. NH3 saturated MeOH/EtOAc)

Sources & evidence

ORD record
ord-c671f41966ad4980a7f7ff6ca386297d
Source dataset
uspto-grants-2002_12
Patent number
US06498177B2

Reaction notes

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