2,3-Dichloro-5,6-dicyano-1,4-benzoquinone → HCID 178456711, compound

HRID 979315Notes

Reaction equation

HRID 979315 reaction equation
[OH:1][C:2]1[CH:15]=[C:14]2[C:5]([NH:6][C:7]3[C:12]([S:13]2(=[O:17])=[O:16])=[CH:11][CH:10]=[CH:9][CH:8]=3)=[C:4]2[CH:18]=[CH:19][CH:20]=[CH:21][C:3]=12.ClC1C(=O)[C:25](C#N)=[C:26]([C:31]#[N:32])C(=O)C=1Cl.C(N)CC>C1COCC1>[CH2:31]([NH:32][C:15]1[C:2](=[O:1])[C:3]2[CH:21]=[CH:20][CH:19]=[CH:18][C:4]=2[C:5]2[C:14]=1[S:13](=[O:17])(=[O:16])[C:12]1[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=1)[N:6]=2)[CH2:26][CH3:25]

Participants

5

Reactant 3

HCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 7852PropylamineHCID 137124805-Hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide

Product 1

HCID 178456711HCID 178456711, compoundYield 62.8%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 5-hydroxy-12H-benzo[a]phenothiazine-7,7-dioxide (594 mg) in THF (10 ml) was added 2,3-dichloro 5,6-dicyano-1,4-benzoquinone (1.021 gram). The mixture was stirred at room temperature for 2 minutes, then there was added n-propyl amine (0.2 ml). The stirring was continued for 0.5 hour, then the mixture was evaporated to dryness. To the residue was added 50 ml dichloromethane and the mixture was stirred for 15 minutes and filtered. The filtrate was evaporated to dryness and the residue crystallized from a mixture of toluene and hexane to afford the title compound (442 mg) as a red-brown crystalline solid, m.p. 149°-151° C. (dec.).

Workup

  1. waitThe stirring was continued for 0.5 hour
  2. customthe mixture was evaporated to dryness
  3. additionTo the residue was added 50 ml dichloromethane
  4. stirringthe mixture was stirred for 15 minutes
  5. filtrationfiltered
  6. customThe filtrate was evaporated to dryness
  7. customthe residue crystallized from a mixture of toluene and hexane

Sources & evidence

ORD record
ord-4c457c88b89346088d00c22d419648ef
Source dataset
uspto-grants-1987_05
Patent number
US04667032

Reaction notes

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