Sodium Carbonate → Anthraquinone

HRID 2071896Notes

Reaction equation

HRID 2071896 reaction equation
C1(N[C:8]2[C:21]3[C:20](=[O:22])[C:19]4[C:14](=[CH:15][C:16](S(O)(=O)=O)=[CH:17][CH:18]=4)[C:13](=[O:27])[C:12]=3[CH:11]=[CH:10][C:9]=2S(O)(=O)=O)C=CC=CC=1.NC1C2C(=O)C3C(=CC(S(O)(=O)=O)=CC=3)C(=O)C=2C(Br)=CC=1S(O)(=O)=O.ClC1N=C(Cl)N=C(Cl)C=1Cl.C(=O)([O-])[O-].[Na+].[Na+]>O>[CH:15]1[C:14]2[C:13](=[O:27])[C:12]3[C:21](=[CH:8][CH:9]=[CH:10][CH:11]=3)[C:20](=[O:22])[C:19]=2[CH:18]=[CH:17][CH:16]=1

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 156902,4,5,6-TetrachloropyrimidineHCID 95105201-Amino-4-bromo-9,10-dioxo-9,10-dihydroanthracene-2,6-disulfonic acidHCID 86735077HCID 86735077, compound

Product 1

HCID 6780Anthraquinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

73.6 g of 1-amino-4-[3',4' -dimethyl-5'-(3"-aminophenyl-1")-disulphimido]-phenylamino-anthraquinone-2,6-disulphonic acid (produced from 1-amino-4-bromoanthraquinone-2,6-disulphonic acid and 3,3'-diamino-5,6-dimethyldibenzene-disulphimide analogously to the data in Example 1) are dissolved in 1300 ml of water and to the solution are added 22.9 g of tetrachloropyrimidine at 80°-85°. The reaction mixture is stirred at 80°-85° the reaction is completed. The pH-value is maintained at 6-7 by the addition of 20% sodium carbonate solution. As soon as the reaction is completed, the dyestuff solution is filtered and the dyestuff then precipitated by the addition of 230 g of solid sodium chloride. The dyestuff is filtered off, subsequently washed with 20% sodium chloride solution and dried in vacuo at 80°. It corresponds to the formula: ##STR35## If, instead of 1-amino-4-[3',4'-dimethyl-5'-(3"-aminophenyl-1")-disulphimido]-phenylamino-anthraquinone-2,6-disulphonic acid, equivalent amounts are used of the aminoanthraquinone dyestuffs, given in Table II, Column II, or of the stated mixtures and, instead of tetrachloropyrimidine, the acylating agents given in Column III, the procedure being otherwise as described in the example and at temperatures given in Column IV then similarly valuable blue reactive anthraquinone dyestuffs are obtained.

Workup

  1. filtrationthe dyestuff solution is filtered
  2. customthe dyestuff then precipitated by the addition of 230 g of solid sodium chloride
  3. filtrationThe dyestuff is filtered off
  4. washsubsequently washed with 20% sodium chloride solution
  5. customdried in vacuo at 80°

Sources & evidence

ORD record
ord-24bf229f6bd54af2989be345d5db6ae8
Source dataset
uspto-grants-1977_09
Patent number
US04049656

Reaction notes

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