Hydrochloric Acid → Triphenylmethane

HRID 396100Notes

Reaction equation

HRID 396100 reaction equation
CN(C)[C:3]1[CH:10]=[CH:9][C:6]([CH:7]=O)=[CH:5][CH:4]=1.NC(N)=O.Cl.[C:17]1(=O)[CH:22]=[CH:21][C:20](=O)[CH:19]=[CH:18]1>>[C:6]1([CH:7]([C:3]2[CH:10]=[CH:9][CH:6]=[CH:5][CH:4]=2)[C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:9]=[CH:10][CH:3]=[CH:4][CH:5]=1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 1176UreaHCID 4650QuinoneHCID 74794-(Dimethylamino)Benzaldehyde

Product 1

HCID 10614Triphenylmethane

Conditions

Temperature
100 °C

Procedure

1000 parts of the intermediate from Example 1 was charged to a flask containing 66 parts of p-dimethylaminobenzaldehyde and 14 parts of urea. To this mixture was charged 90 parts of muriatic acid over a 5 minute period. This mixture was allowed to heat up to 95-105° C., and maintained at this temperature overnight. At the end of the hold period, the reaction mixture was allowed to cool to 75° C., and 120 parts of p-benzoquinone was added. The mixture was allowed to stir for 1.5 hrs maintaining a temperature of 75-85° C. The acid is neutralized with a caustic solution, the product washed with water, and dried. A UV/VIS spectrum of the bright mid range blue product shows a lambda max absorbances at 548 nm and 607 nm in toluene.

Workup

  1. temperaturemaintained at this temperature overnight
  2. temperatureto cool to 75° C.
  3. temperaturemaintaining a temperature of 75-85° C
  4. washthe product washed with water
  5. customdried

Sources & evidence

ORD record
ord-d5730b7b1aa64a64afe3aa86e24c7234
Source dataset
uspto-grants-2003_08
Patent number
US06607588B2

Reaction notes

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