Chloranil → HCID 19899013, compound

HRID 1196663Notes

Reaction equation

HRID 1196663 reaction equation
P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:2].ClC1C(=O)C(Cl)=C(Cl)C(=O)C=1Cl.[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]([NH2:47])=[C:35]2[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([O:44][CH3:45])=[O:43])[CH2:37][C:36]2=O)=[CH:30][CH:29]=1>C1C=CC=CC=1>[Cl:27][C:28]1[CH:33]=[CH:32][C:31]([C:34]2[C:35]3[CH2:41][CH2:40][CH2:39][CH:38]([C:42]([O:44][CH3:45])=[O:43])[CH2:37][C:36]=3[S:2][N:47]=2)=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 8371ChloranilHCID 14817Phosphorus sulfide (P2S5)HCID 54297546HCID 54297546, compound

Product 1

HCID 19899013HCID 19899013, compoundYield 34.5%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

2 g of dry diatomaceous earth were stirred in 15 ml of dry benzene and 2 g (9 mmol) of phosphorus pentasulfide and 0.4 g (1.6 mmol) of 2,3,5,6-tetrachloro-p-benzoquinone was added. 0.5 g (1.62 mmol) of methyl 4-[(4-chlorophenyl)(amino)methylene]-3-oxocycloheptanecarboxylate was added and the mixture was heated under reflux for 0.5 hour. The mixture was filtered and the filter cake was washed with six 20 ml portions of hot ethyl acetate. The combined filtrate and washings were evaporated and the residue, after chromatography on silica gel using 30% ethyl acetate/hexane for the elution and recrystallization from methylcyclohexane, gave 0.18 g of methyl 3-(4-chlorophenyl)-5,6,7,8-tetrahydro-4H-cyclohept[d]isothiazole-7-carboxylate of melting point 108°-109° C.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 0.5 hour
  3. filtrationThe mixture was filtered
  4. washthe filter cake was washed with six 20 ml portions of hot ethyl acetate
  5. customThe combined filtrate and washings were evaporated
  6. washthe residue, after chromatography on silica gel using 30% ethyl acetate/hexane for the elution and recrystallization from methylcyclohexane

Sources & evidence

ORD record
ord-81e5f181bf4b4723aa3f266cb6599108
Source dataset
uspto-grants-1992_05
Patent number
US05114960

Reaction notes

Loading…