Acetone → Auramine

HRID 1076061Notes

Reaction equation

HRID 1076061 reaction equation
[CH3:1][N:2]([C:4]1[CH:9]=[CH:8][C:7]([C:10]([C:12]2[CH:17]=[CH:16][C:15]([N:18]([CH3:20])[CH3:19])=[CH:14][CH:13]=2)=[NH:11])=[CH:6][CH:5]=1)[CH3:3].Cl.CC(C)=O>O>[CH3:20][N:18]([C:15]1[CH:14]=[CH:13][C:12]([C:10]([C:7]2[CH:6]=[CH:5][C:4]([N:2]([CH3:3])[CH3:1])=[CH:9][CH:8]=2)=[NH:11])=[CH:17][CH:16]=1)[CH3:19]

Participants

4

Reactant 2

HCID 180AcetoneHCID 17170Auramine hydrochloride

Product 1

HCID 10298Auramine

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

321.5 parts of Auramine O are put in suspension, whilst being stirred, in 680 parts of acetone and 140 parts of water. 340 parts by weight of 30% soda are added to this suspension. The temperature rises from 20°/22°C. to 35°C. A transition to solution is then observed, following by precipitation of the Auramine base in crystalline form. The mixture is allowed to return to ambient temperature, is cooled to 0°-5°C. for 4 hours, filtered and washed twice with 400 parts by weight of 50% acetonewater mixture. The filtered material is then dried at 70°-80°C. for 24 hours and 212 parts of Auramine O base with a melting point of 135°-136°C. are obtained. (The theoretical melting point is 136°C.)

Workup

  1. addition340 parts by weight of 30% soda are added to this suspension
  2. customrises from 20°
  3. custom22°C. to 35°C
  4. customfollowing by precipitation of the Auramine base in crystalline form
  5. customto return to ambient temperature
  6. temperatureis cooled to 0°-5°C. for 4 hours
  7. filtrationfiltered
  8. washwashed twice with 400 parts by weight of 50% acetonewater mixture
  9. customThe filtered material is then dried at 70°-80°C. for 24 hours

Sources & evidence

ORD record
ord-44ea1845bebe4e66916349e30463a190
Source dataset
uspto-grants-1976_05
Patent number
US03954864

Reaction notes

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