Carbon Disulfide → HCID 14796551, compound

HRID 1588867Notes

Reaction equation

HRID 1588867 reaction equation
[OH:1][C:2]1([C:15](OC)=[O:16])[C:14]2[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=2[C:8]2[C:3]1=[CH:4][CH:5]=[CH:6][CH:7]=2.CC(C)([O-])C.[K+].[C:25](=[S:27])=S.ClC(OCC)=O.[C:34]1([NH:40][NH2:41])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1>O1CCCC1>[C:34]1([NH:40][N:41]2[C:15](=[O:16])[C:2]3([C:3]4[CH:4]=[CH:5][CH:6]=[CH:7][C:8]=4[C:9]4[C:14]3=[CH:13][CH:12]=[CH:11][CH:10]=4)[O:1][C:25]2=[S:27])[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=1

Participants

7

Reactant 5

HCID 6348Carbon DisulfideHCID 7516PhenylhydrazineHCID 10928Ethyl chloroformateHCID 267210Methyl 9-hydroxy-9H-fluorene-9-carboxylateHCID 23665647Potassium tert-butoxide

Product 1

HCID 14796551HCID 14796551, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 9-hydroxy-9-fluorenecarboxylic acid, methyl ester (8.91 g, 0.0371 mole) in tetrahydrofuran (89 ml) was treated with potassium tert.-butoxide (4.16 g, 0.0371 mole). After 6 minutes the solution was cooled in an ice bath and carbon disulfide (2.3 ml, 0.038 mole) was added. After 7 minutes ethyl chloroformate (3.6 ml, 0.038 mole) was added to the cold solution. After 7 minutes 97% phenylhydrazine (3.9 ml, 0.038 mole) was added. After 3 minutes, the mixture was evaporated under reduced pressure to a yellow syrup. The syrup was treated with 1-chlorobutane and water, and the organic layer was washed with saturated sodium bicarbonate solution, water, 1N HCl, and water. The dried (magnesium sulfate) solution was filtered and evaporated under reduced pressure to an oil. The oil was crystallized from carbon tetrachloride/hexane, and the solid product further purified by boiling with isopropanol (without dissolution of all solid), cooling, and filtering. The product was obtained as 3.56 g (27% of theoretical) of analytically-pure white solid, m.p. 187°-189° C.

Workup

  1. temperatureAfter 6 minutes the solution was cooled in an ice bath
  2. customthe mixture was evaporated under reduced pressure to a yellow syrup
  3. additionThe syrup was treated with 1-chlorobutane and water
  4. washthe organic layer was washed with saturated sodium bicarbonate solution, water, 1N HCl, and water
  5. dry with materialThe dried (magnesium sulfate) solution
  6. filtrationwas filtered
  7. customevaporated under reduced pressure to an oil
  8. customThe oil was crystallized from carbon tetrachloride/hexane
  9. customthe solid product further purified
  10. dissolutionwithout dissolution of all solid),
  11. temperaturecooling
  12. filtrationfiltering
  13. customThe product was obtained as 3.56 g (27% of theoretical) of analytically-pure white solid, m.p. 187°-189° C.

Sources & evidence

ORD record
ord-7aa1594600394e4fb68e744f69f78c14
Source dataset
uspto-grants-1993_06
Patent number
US05223523

Reaction notes

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