p-Toluenesulfonic acid → HCID 178441038, compound

HRID 2164708Notes

Reaction equation

HRID 2164708 reaction equation
[CH2:1]([C@H:5]1[CH2:10][CH2:9][C@H:8]([OH:11])[CH2:7][CH2:6]1)[CH2:2][CH2:3][CH3:4].C1(C)C=CC(S(O)(=O)=O)=CC=1.[NH2:23][C:24]1([CH:49]=[CH:48][C:47]([CH2:50][CH2:51][CH2:52][CH3:53])=[CH:46][CH2:45]1)[NH:25][C:26]1[C:39]2[C:38](=[O:40])[C:37]3[C:32](=[CH:33][CH:34]=[CH:35][CH:36]=3)[C:31](=[O:41])[C:30]=2[CH:29]=[CH:28][C:27]=1[C:42](O)=[O:43]>ClC1C=CC=CC=1Cl>[CH2:1]([C@H:5]1[CH2:6][CH2:7][C@H:8]([O:11][C:42]([C:27]2[CH:28]=[CH:29][C:30]3[C:31](=[O:41])[C:32]4[C:37](=[CH:36][CH:35]=[CH:34][CH:33]=4)[C:38](=[O:40])[C:39]=3[C:26]=2[NH:25][C:24]2([NH2:23])[CH:45]=[CH:46][C:47]([CH2:50][CH2:51][CH2:52][CH3:53])=[CH:48][CH2:49]2)=[O:43])[CH2:9][CH2:10]1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 704026481-Amino-4-n-butylanilinoanthraquinone-2-carboxylic acidHCID 178445814HCID 178445814, compound

Product 1

HCID 178441038HCID 178441038, compoundYield 46.4%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

To 200 ml of orthodichlorobenzene were added 31.6 g of trans-4-n-butylcyclohexanol, 5.6 g of p-toluenesulfonic acid, and 28 g of 1-amino-4-n-butylanilinoanthraquinone-2-carboxylic acid. The mixture was heated slowly to 110° to 115° C. and maintained at this temperature for 17 hours with stirring. The orthochlorobenzene solution was concentrated to 70 ml under reduced pressure, and 1500 ml of methanol was added. The resulting precipitates was filtered out and then purified by column chromatography wherein silica gel was used as a carrier and chloroform was used as a solvent to obtain 17.3 g of 1-amino-4-n-butylanilinoanthraquinone-2-carboxylic acid-trans-4-n-butylcyclohexyl ester.

Workup

  1. temperatureThe mixture was heated slowly to 110° to 115° C.
  2. temperaturemaintained at this temperature for 17 hours
  3. concentrationThe orthochlorobenzene solution was concentrated to 70 ml under reduced pressure, and 1500 ml of methanol
  4. additionwas added
  5. customThe resulting precipitates
  6. filtrationwas filtered out
  7. custompurified by column chromatography wherein silica gel

Sources & evidence

ORD record
ord-c59d58e7bcc341988eed93288b59ff2a
Source dataset
uspto-grants-1985_03
Patent number
US04507221

Reaction notes

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