Acetic Acid → HCID 178527822, compound

HRID 895136Notes

Reaction equation

HRID 895136 reaction equation
[NH2:1][C:2]1[C:7](Br)=[CH:6][C:5]([Cl:9])=[CH:4][N:3]=1.[K+].C(O[C:14]([S-:16])=[S:15])C.O.C(O)(=O)C>CN1CCCC1=O>[Cl:9][C:5]1[CH:6]=[C:7]2[S:15][C:14]([SH:16])=[N:1][C:2]2=[N:3][CH:4]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 962WaterHCID 2735045Potassium ethylxanthateHCID 27639713-Bromo-5-chloropyridin-2-amine

Product 1

HCID 178527822HCID 178527822, compoundYield 98%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A solution of 133 g (0.64 mol) of 2-amino-3-bromo-5-chloropyridine from Example 1.1 in 1.02 l of N-methylpyrrolidone was admixed with 205 g (1.28 mol) O-ethylxanthic acid potassium salt. The reaction mixture was refluxed for 6 h and then allowed to cool to ambient temperature. 2.7 l of demineralized water were added then acetic acid to adjust the reaction mixture to pH 4.5. The resulting precipitate was filtered, washed with demineralized water (2×600 ml). The solid was triturated in succession with demineralized water (2×4.2 l) and ethanol, (1.5 l), filtered, washed with ethanol (2×300 ml) followed by hexane (2×400 ml) and dried in vacuo at 45° C. to give 127 g (yield: 98%) of 6-chloro-2-mercaptothiazolo[4,5-b]pyridine used without further purification.

Workup

  1. temperatureThe reaction mixture was refluxed for 6 h
  2. filtrationThe resulting precipitate was filtered
  3. washwashed with demineralized water (2×600 ml)
  4. customThe solid was triturated in succession with demineralized water (2×4.2 l) and ethanol, (1.5 l)
  5. filtrationfiltered
  6. washwashed with ethanol (2×300 ml)
  7. customdried in vacuo at 45° C.

Sources & evidence

ORD record
ord-b9f0ed74bab340c5a91a3ea75d885667
Source dataset
uspto-grants-2005_07
Patent number
US06914068B2

Reaction notes

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