p-Toluenesulfonic acid → HCID 19360973、化合物

HRID 376229

反応式

HRID 376229 の反応式
[C:1]([C:5]1[C:6]([SH:16])=[C:7]([CH:9]=[C:10]([C:12]([CH3:15])([CH3:14])[CH3:13])[CH:11]=1)[NH2:8])([CH3:4])([CH3:3])[CH3:2].C(C1C=[C:23]([CH:27]=C(C(C)(C)C)C=1)[C:24]([OH:26])=[O:25])(C)(C)C.[C:34]1(C)C=CC(S(O)(=O)=O)=C[CH:35]=1>CO>[C:12]([C:10]1[CH:11]=[C:5]([C:1]([CH3:4])([CH3:3])[CH3:2])[C:6]2[S:16][C:27]([CH2:23][C:24]([O:26][CH2:34][CH3:35])=[O:25])=[N:8][C:7]=2[CH:9]=1)([CH3:15])([CH3:14])[CH3:13]

参加物

5

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 853393,5-Bis(tert-butyl)benzoic acidHCID 12087014HCID 12087014、化合物

生成物 1

HCID 19360973HCID 19360973、化合物

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

実験手順

A mixture of 40 g of 3,5-di(t-butyl)-2-mercaptoaniline [prepared according to a literature procedure from 3,5-di(t-butyl)benzoic acid] and 75 mL of ethyl 3-(trimethoxy)propionate in 1.2 L of methanol containing 1.5 g of p-toluenesulfonic acid was stirred at r.t. for 18 h. Excess methanol was removed by rotary evaporation. The precipitated the solid was filtered and washed with cold methanol. The crude product was purified by flash chromatography on silica gel and eluted with heptane to give 20 g of ethyl 2-[5,7-di(t-butyl)benzothiazolyl]acetate. The latter was refluxed with 16 g of 1,1,7,7-tetramethyl-8-hydroxy-9-formyljulolidine in 200 mL of acetonitrile containing 4 mL of piperidine for 18 h. The reaction mixture was cooled and the precipitated bright orange solid was filtered to give 13 g of the desired dye C-545TB: m.p. 275-276° C.; Tg=140° C.

後処理

  1. customprepared
  2. customExcess methanol was removed by rotary evaporation
  3. customThe precipitated the solid
  4. filtrationwas filtered
  5. washwashed with cold methanol
  6. customThe crude product was purified by flash chromatography on silica gel
  7. washeluted with heptane

出典と根拠

ORDレコード
ord-7b439c4485154a7787245cc35d75960c
出典データセット
uspto-grants-2000_02
特許番号
US06020078

関連ノート

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