p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1164324ノート

反応式

HRID 1164324 の反応式
S=C1C2C=CC=C3C=2C(=CC=C3)N1CC(O)=O.NC(O)C.O.[C:23]1([CH3:33])[CH:28]=[CH:27][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:25][CH:24]=1>C1C=CC=CC=1>[CH3:33][C:23]1[CH:24]=[CH:25][C:26]([S:29]([OH:32])(=[O:31])=[O:30])=[CH:27][CH:28]=1

参加物

5

反応物 3

HCID 521998p-Toluenesulfonic acid monohydrateHCID 522583Acetaldehyde ammoniaHCID 3069842Benz(cd)indole-1(2H)-acetic acid, 2-thioxo-

生成物 1

HCID 6101p-Toluenesulfonic acid

試薬・触媒・溶媒 1

HCID 241Benzene溶媒

実験手順

A suspension of 2-thioxo-benz[cd]indole-1(2H)-acetic acid (1.0 g, 4.11 mmol, described in Example 6) aminoethanol (0.5 g, 0.49 mL, 8.22 mmol) and p-toluenesulfonic acid hydrate (1.88 g, 9.86 mmol) in benzene (50 mL) was refluxed for 48 hr with stirring in a Soxhlet apparatus containing a thimble filled with 3A molecular sieves. The mixture was evaporated to dryness, and the residue was triturated with cold water (50 mL). The precipitate was collected by filtration, washed with diethyl ether (50 mL), and crystallized from water to give the 4-methylphenylsulfonic acid salt of the title compound (1.0 g): Anal. Calcd for C15H14N2O2S.C7H8O3S: C, 57.63% H, 4.84% N, 6.11% and Found: C, 57.58% H, 4.94% N, 6.23%; IR (mineral oil) 2900, 1740, 1375, and 11700 cm-1 ; UV max (methanol) 342 (ε3400), 310 (6700), 304 (6740), 267 (27,900), 259 (21,580), and 218 nm (26,210); NMR (DMSO-d6)ε 2.25 (s, 3H), 3.12 (t, 2H), 4.32 (t, 2H), 5.3 (s, 2H), 7.7 (m, 10H), and 7.9 (s, 3H).

後処理

  1. temperaturewas refluxed for 48 hr
  2. additioncontaining a thimble
  3. customThe mixture was evaporated to dryness
  4. customthe residue was triturated with cold water (50 mL)
  5. filtrationThe precipitate was collected by filtration
  6. washwashed with diethyl ether (50 mL)
  7. customcrystallized from water

出典と根拠

ORDレコード
ord-189ad8fc91614b02bd36873957e31cb7
出典データセット
uspto-grants-1983_01
特許番号
US04369188

反応ノート

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