Carbon Disulfide → HCID 178527938, compound

HRID 452588Notes

Reaction equation

HRID 452588 reaction equation
FC(F)(F)C(O)=O.[S:8]1[C:12]2[CH:13]=[C:14]([C:17]([NH:19][NH2:20])=[O:18])[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1.[C:21](=S)=[S:22].C(N(CC)CC)C>C(O)C.C(OCC)(=O)C.O1CCCC1>[S:8]1[C:12]2[CH:13]=[C:14]([C:17]3[O:18][C:21]([SH:22])=[N:20][N:19]=3)[CH:15]=[CH:16][C:11]=2[N:10]=[CH:9]1

Participants

6

Reactant 3

HCID 6348Carbon DisulfideHCID 8471TriethylamineHCID 686638551,3-Benzothiazole-6-carbohydrazide trifluoroacetate

Product 1

HCID 178527938HCID 178527938, compoundYield 83%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 21939870Tetrahydrofuran ethyl acetateSolvent

Procedure

A suspension of benzothiazole-6-carbohydrazide trifluoroacetate (4.92 g, 16.0 mmol), carbon disulfide (2.41 mL, 40.0 mmol) and triethylamine (5.58 mL, 40.0 mmol) in ethanol (60 mL) was heated under reflux for 1.5 hr. After cooling, the reaction mixture was diluted with ethyl acetate/tetrahydrofuran, washed with 1M hydrochloric acid and water, and concentrated under reduced pressure. The residue was recrystallized from tetrahydrofuran to give the title compound (3.11 g, yield 83%) as pale-yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 1.5 hr
  3. temperatureAfter cooling
  4. washwashed with 1M hydrochloric acid and water
  5. concentrationconcentrated under reduced pressure
  6. customThe residue was recrystallized from tetrahydrofuran

Sources & evidence

ORD record
ord-ffb7885347f742fab940f6c28f325a49
Source dataset
uspto-grants-2013_07
Patent number
US08492378B2

Reaction notes

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