p-Toluenesulfonic acid → HCID 19360973, compound

HRID 376229

Reaction equation

HRID 376229 reaction equation
[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]

Participants

5

Reactant 3

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

Product 1

HCID 19360973HCID 19360973, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-7b439c4485154a7787245cc35d75960c
Source dataset
uspto-grants-2000_02
Patent number
US06020078

Linked notes

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