Thiophenol → HCID 19770638, compound

HRID 1589880Notes

Reaction equation

HRID 1589880 reaction equation
[C:1]1([SH:7])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:8](=[O:11])([O-])[O-].[K+].[K+].Cl[C:15]1[C:28]2[C:27](=[O:29])[C:26]3[C:21](=[C:22](Cl)[CH:23]=[CH:24][C:25]=3[N+]([O-])=O)[C:20](=[O:34])[C:19]=2[C:18]([N+]([O-])=O)=[CH:17][CH:16]=1.[OH:38][C:39]1[CH:44]=[CH:43][C:42]([SH:45])=[CH:41][CH:40]=1>CN(C)C=O.O>[OH:38][C:39]1[CH:44]=[CH:43][C:42]([S:45][C:15]2[C:28]3[C:27](=[O:29])[C:26]4[C:21](=[C:22]([S:7][C:1]5[CH:6]=[CH:5][C:8]([OH:11])=[CH:3][CH:2]=5)[CH:23]=[CH:24][C:25]=4[S:7][C:1]4[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=4)[C:20](=[O:34])[C:19]=3[C:18]([S:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)=[CH:17][CH:16]=2)=[CH:41][CH:40]=1

Participants

7

Reactant 4

HCID 7969ThiophenolHCID 11430Potassium CarbonateHCID 2355621,5-dichloro-4,8-dinitroanthracene-9,10-dioneHCID 2401474-Mercaptophenol

Product 1

HCID 19770638HCID 19770638, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent3×

Conditions

Temperature
120 °C

Procedure

A mixture of 22 grams (0.2 mole) of benzenethiol, 25.6 grams (0.2 mole) of potassium carbonate in 100 milliliters of dimethyl formamide was heated with stirring to 120° C. for 2 hours. The cooled mixture was added to a cold mixture of 36.6 grams (0.1 mole) of 1,5-dichloro-4,8-dinitroanthraquinone in 150 milliliters of dimethyl formamide, and stirred for 3 hours at room temperature. After addition of 25.6 grams (0.2 mole) of p-hydroxybenzenethiol in 100 milliliters of dimethyl formamide, the mixture was stirred at 125° C. for 2 hours. The resulting reaction mixture was then cooled, and poured slowly into 2 liters of water. Subsequently, the above solid product III was filtered, washed once with water, acetic acid, methanol, respectively, and then dried in vacuo. The yield of this dye was 50 grams (75 percent), m.p. >340° C.; vis (DMF), λmax 540 nm (ε 12,000); Analysis Calculated for C38H24O4S4 : C, 67.83; H, 3.59; O, 9.51; S, 19.06. Found: C, 67.51; H, 3.89; O, 9.35; S, 19.32.

Workup

  1. temperaturewas heated
  2. stirringstirred for 3 hours at room temperature
  3. stirringthe mixture was stirred at 125° C. for 2 hours
  4. customThe resulting reaction mixture
  5. temperaturewas then cooled
  6. filtrationSubsequently, the above solid product III was filtered
  7. washwashed once with water, acetic acid, methanol
  8. customrespectively, and then dried in vacuo

Sources & evidence

ORD record
ord-6f346f78fce546988bd5edab481786b8
Source dataset
uspto-grants-1993_04
Patent number
US05200290

Reaction notes

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