Hydrochloric Acid → HCID 53716635, compound

HRID 1021332Notes

Reaction equation

HRID 1021332 reaction equation
[C:1]1([N:7]([C:14]2[CH:24]=[CH:23][C:17]([CH:18]=[CH:19][C:20](O)=[O:21])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.S(Cl)([Cl:27])=O.CN(C)C=O.Cl>ClCCl>[C:1]1([N:7]([C:14]2[CH:24]=[CH:23][C:17]([CH:18]=[CH:19][C:20]([Cl:27])=[O:21])=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 912584-(Diphenylamino)cinnamic acid

Product 1

HCID 53716635HCID 53716635, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A 50 mL round bottom flask equipped with a magnetic stirrer and a nitrogen inlet-outlet was charged with 4-(N,N-diphenylamino)cinnamic acid (1.0 g, 3.2 mmol) in 15 mL dichloromethane. Thionyl chloride (0.35 mL, 4.8 mmol) was added followed by 12.4 □L N,N-dimethylformamide. Hydrogen chloride gas evolution began immediately and then ceased within one hour of stirring. The solution was stirred for 3 h and then concentrated on a rotary evaporator. The product was transferred to a high vacuum line and residual solvent was removed under vacuum. The product was obtained as a brown solid and stored under nitrogen without any further purification.

Workup

  1. customA 50 mL round bottom flask equipped with a magnetic stirrer and a nitrogen inlet-outlet
  2. stirringThe solution was stirred for 3 h
  3. concentrationconcentrated on a rotary evaporator
  4. customwas removed under vacuum
  5. customThe product was obtained as a brown solid
  6. customstored under nitrogen without any further purification

Sources & evidence

ORD record
ord-d1d57ebbc72245008d91cea73bf76eff
Source dataset
uspto-grants-2014_05
Patent number
US08716697B2

Reaction notes

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