Methanesulfonic Acid → HCID 19785214, compound

HRID 256534Notes

Reaction equation

HRID 256534 reaction equation
O[CH:2]([C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)[CH2:3][N:4]([CH2:6][CH2:7][C:8]1[CH:12]=[CH:11][N:10]([S:13]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)(=[O:15])=[O:14])[CH:9]=1)[CH3:5].CS(O)(=O)=O>FC(F)(F)C(O)=O>[C:16]1([S:13]([N:10]2[C:9]3[CH:2]([C:22]4[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=4)[CH2:3][N:4]([CH3:5])[CH2:6][CH2:7][C:8]=3[CH:12]=[CH:11]2)(=[O:15])=[O:14])[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 6395Methanesulfonic AcidHCID 19785208HCID 19785208, compound

Product 1

HCID 19785214HCID 19785214, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

A mixture of N-(2-hydroxy-2-phenylethyl)-N-methyl-2-(1-phenylsulphonyl-3-pyrrolyl)ethylamine (5.5 g), trifluoroacetic acid (200 ml) and methanesulphonic acid (2.13 g) was refluxed for 2.5 hours. After evaporating to dryness, water then 0.880 ammonia were added and the product was extracted into dichloromethane. The extracts were washed with water, dried and evaporated to give an oil. The oil was purified by chromatography on silica, eluting with chloroform then increasing amounts of methanol (1-5%) in chloroform to give the title product as a solid, m.p. 115°-116° C. (ethanol).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. customAfter evaporating to dryness, water
  3. addition0.880 ammonia were added
  4. extractionthe product was extracted into dichloromethane
  5. washThe extracts were washed with water
  6. customdried
  7. customevaporated
  8. customto give an oil
  9. customThe oil was purified by chromatography on silica
  10. washeluting with chloroform

Sources & evidence

ORD record
ord-eabcd6cbfc7b46729c9fffe347463ac0
Source dataset
uspto-grants-1993_11
Patent number
US05258378

Reaction notes

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