Thiophenol → HCID 19770638, compound

HRID 236616Notes

Reaction equation

HRID 236616 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. The above solid product III was filtered, washed once each with water, acetic acid, methanol and then dried in vacuo. The yield of this red dye was 50 grams (75%), m.p.>340° C.; vis (DMF), λmax 540 nm (ε12,000); Anal. Calcd. for C 38 H24O4S4 : 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. filtrationThe above solid product III was filtered
  7. washwashed once each with water, acetic acid, methanol
  8. customdried in vacuo

Sources & evidence

ORD record
ord-55911b73e3074ea3b4a6f842af6b5569
Source dataset
uspto-grants-1987_02
Patent number
US04645727

Reaction notes

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