Ethylamine → HCID 86747813, compound

HRID 1033081Notes

Reaction equation

HRID 1033081 reaction equation
[CH2:1]([O:3][CH2:4][CH:5]1[S:10](=[O:12])(=[O:11])[C:9]2[S:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:8]=2[CH:7](O)[CH2:6]1)[CH3:2].C1(C)C=CC(S(Cl)(=O)=O)=CC=1.[CH2:32]([NH2:34])[CH3:33]>N1C=CC=CC=1>[CH2:1]([O:3][CH2:4][C@H:5]1[S:10](=[O:12])(=[O:11])[C:9]2[S:13][C:14]([S:16]([NH2:19])(=[O:18])=[O:17])=[CH:15][C:8]=2[C@@H:7]([NH:34][CH2:32][CH3:33])[CH2:6]1)[CH3:2]

Participants

5

Reactant 3

HCID 6341Ethylamine2×HCID 73974-Toluenesulfonyl chlorideHCID 67692704HCID 67692704, compound

Product 1

HCID 86747813HCID 86747813, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
-10 °C

Procedure

5,6-Dihydro-6-ethoxymethyl-4-hydroxy-4H-thieno[2,3-b]thiopyran-2-sulfonamide-7,7-dioxide (4.25 g, 0.0123 mol) was dissolved in dry pyridine (25 ml) and the solution was cooled to -10° C. p-Toluenesulfonyl chloride (5.14 g, 0.027 mol) was added and the mixture was stirred at -10° C. for 5 hours. Anhydrous ethylamine (26 ml, 0.4 mol) was added and the mixture was stirred for 2 hours at room temperature. Finally, 70% ethylamine (32 ml. 0.40 mol) was added and the mixture was heated at 50° C. overnight. The dark mixture was concentrated in vacuo and the residual oil was taken up in ethyl acetate (100 ml) and saturated sodium bicarbonate (100 ml). The aqueous layer was separated and extracted with ethyl acetate. The combined ethyl, acetate solutions were washed with saturated sodium chloride, dried, filtered and concentrated in vacuo. The oil obtained was a 2:1 mixture of cis and trans isomers which were separated by silica gel chromatography using 7.5% methanol-chloroform. Total recovery was 2.43 g. Yield of 33 was 54%.

Workup

  1. additionwas added
  2. stirringthe mixture was stirred for 2 hours at room temperature
  3. temperaturethe mixture was heated at 50° C. overnight
  4. concentrationThe dark mixture was concentrated in vacuo
  5. customThe aqueous layer was separated
  6. extractionextracted with ethyl acetate
  7. washThe combined ethyl, acetate solutions were washed with saturated sodium chloride
  8. customdried
  9. filtrationfiltered
  10. concentrationconcentrated in vacuo
  11. customThe oil obtained
  12. additiona 2:1 mixture of cis and trans isomers which
  13. customwere separated by silica gel chromatography

Sources & evidence

ORD record
ord-5671a578672c475ab5551ad987a853fd
Source dataset
uspto-grants-1994_05
Patent number
US05308863

Reaction notes

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