1-Pentanol → HCID 23316292, compound

HRID 1982497Notes

Reaction equation

HRID 1982497 reaction equation
[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([N+]([O-])=O)=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22].NC1C2C(=O)C3C(=CC=CC=3)C(=O)C=2C([N+]([O-])=O)=CC=1C(Cl)=O.C(O)CCCC.C(=O)([O-])[O-].[K+].[K+].[CH3:64][C:65]1[CH:70]=[CH:69][C:68]([SH:71])=[CH:67][CH:66]=1>O.CN1CCCC1=O>[NH2:1][C:2]1[C:15]2[C:14](=[O:16])[C:13]3[C:8](=[CH:9][CH:10]=[CH:11][CH:12]=3)[C:7](=[O:17])[C:6]=2[C:5]([S:71][C:68]2[CH:69]=[CH:70][C:65]([CH3:64])=[CH:66][CH:67]=2)=[CH:4][C:3]=1[C:21]([O:23][CH2:24][CH2:25][CH2:26][CH2:27][CH3:28])=[O:22]

Participants

8

Reactant 5

HCID 62761-PentanolHCID 78114-MethylbenzenethiolHCID 11430Potassium CarbonateHCID 144386121-Amino-9,10-dihydro-4-nitro-9,10-dioxo-2-anthracenecarbonyl chlorideHCID 23316281HCID 23316281, compound

Product 1

HCID 23316292HCID 23316292, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

7.7 g of pentyl 1-amino-4-nitroanthraquinone-2-carboxylate, prepared from 1-amino-4-nitroanthraquinone-2-carboxylic acid chloride and n-pentanol, 2.7 g of anhydrous potassium carbonate and 2.7 g of 4-methylthiophenol are introduced into 50 cc of N-methylpyrrolidone, and the mixture is heated to 125°-130° C. in the course of 1 hour and is stirred at this temperature until, after about 1.5 hours, complete reaction has been achieved. The reaction mixture is allowed to cool and is diluted at 40° C. with 20 cc of water. When the mixture has cooled completely, the dyestuff which has been precipitated is filtered off with suction and washed with a mixture of N-methylpyrrolidone and water and then with hot water. After drying at 60° C., 6.7 g of n-pentyl 1-amino-4-(4-methylphenylmercapto)-anthraquinone-2-carboxylate are obtained, corresponding to a yield of 72% of theory. The dyestuff can be purified by recrystallisation from dimethylformamide.

Workup

  1. temperaturethe mixture is heated to 125°-130° C. in the course of 1 hour
  2. customcomplete reaction
  3. temperatureto cool
  4. temperatureWhen the mixture has cooled completely
  5. customthe dyestuff which has been precipitated
  6. filtrationis filtered off with suction
  7. washwashed with a mixture of N-methylpyrrolidone and water
  8. customAfter drying at 60° C.

Sources & evidence

ORD record
ord-f8fd27e4a6db450da0152ad4b73115d1
Source dataset
uspto-grants-1986_06
Patent number
US04596666

Reaction notes

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