Water → HCID 20541427, compound

HRID 1065092Notes

Reaction equation

HRID 1065092 reaction equation
[S:1]([OH:11])(=[O:10])([C:3]1[CH:8]=[CH:7][C:6]([NH2:9])=[CH:5][CH:4]=1)=[O:2].O.O.O.O.C([O-])(=O)C.[Na+].[CH3:21][CH:22]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28]Cl)=[CH:26][CH:25]=1)[CH3:23]>C(#N)C>[CH3:21][CH:22]([C:24]1[CH:31]=[CH:30][C:27]([CH2:28][NH:9][C:6]2[CH:5]=[CH:4][C:3]([S:1]([OH:11])(=[O:10])=[O:2])=[CH:8][CH:7]=2)=[CH:26][CH:25]=1)[CH3:23]

Participants

6

Reactant 4

HCID 962WaterHCID 8479Sulfanilic acidHCID 749164-Isopropylbenzyl chlorideHCID 23665404Sodium Acetate Trihydrate

Product 1

HCID 20541427HCID 20541427, compoundYield 20.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent3×

Conditions

Temperature
65 °C

Procedure

To a 1-liter (1) 3-necked round-bottomed flask equipped with an overhead stirrer, reflux condenser and dropping funnel and containing a stirred mixture of 52.0 g (0.30 mole) of sulfanilic acid in 225 ml of warm (~65° C.) water was added 83.0 g (0.61 mole) of sodium acetate trihydrate and 75 ml of acetonitrile. The temperature of the resulting yellow solution was stabilized at about 70° C. and a solution of 33.8 g (0.20 mole) of 4-(1-methylethyl)benzyl chloride in 75 ml of acetonitrile was added over 70 minutes. The solution was then refluxed for an additional 31/2 hrs, and 95 ml of acetonitrile was removed by distillation over a 30 minute period, during which time 50 ml of concentrated hydrochloric acid (con. HCl) was added dropwise. The resulting mixture was filtered hot (~80° C.) and the collected solids were slurried in 300 ml of boiling methanol for 15 min. and then vacuum filtered. The slurrying and vacuum filtration process was repeated first with 300 ml of warm (65° C.) water and then again with 300 ml of boiling methanol. Air-drying of the collected solids gave 12.51 g (20.5% yield) of purified 4-(((4-(1-methylethyl)phenyl)methyl)amino)benzenesulfonic acid as a white powder, having a melting point greater than 275° C.

Workup

  1. temperaturereflux condenser
  2. additioncontaining
  3. customwas stabilized at about 70° C.
  4. customwas removed by distillation over a 30 minute period, during which time 50 ml of concentrated hydrochloric acid (con. HCl)
  5. additionwas added dropwise
  6. filtrationThe resulting mixture was filtered hot (~80° C.)
  7. filtrationvacuum filtered
  8. filtrationThe slurrying and vacuum filtration process
  9. customAir-drying of the collected solids

Sources & evidence

ORD record
ord-fbf6b5c4f4464f9883c85a6d6764f083
Source dataset
uspto-grants-1982_05
Patent number
US04328244

Reaction notes

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