Isethionic Acid → HCID 131710445, compound

HRID 1284284Notes

Reaction equation

HRID 1284284 reaction equation
[CH3:1][C:2]([NH2:22])([CH3:21])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:20])([F:19])[C:10]([F:18])([F:17])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[S:23]([CH2:27][CH2:28][OH:29])([OH:26])(=[O:25])=[O:24]>C(O)(C)C>[CH3:21][C:2]([NH2:22])([CH3:1])[C:3]1[CH:8]=[CH:7][C:6]([C:9]([F:19])([F:20])[C:10]([F:17])([F:18])[C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:5][CH:4]=1.[S:23]([CH2:27][CH2:28][OH:29])([O-:26])(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 7866Isethionic AcidHCID 176160alpha,alpha-Dimethyl-4-(alpha,alpha,beta,beta-tetrafluorophenethyl)benzylamine

Product 1

HCID 131710445HCID 131710445, compound

Reagents, catalysts & solvents 1

HCID 3776IsopropanolSolvent

Procedure

α,α-Dimethyl-4-(α,α,β,β-tetrafluorophenethyl)-benzylamine, 4.1 g. (0.0132 mole), was dissolved in 20 ml. of isopropyl alcohol and the solution treated with 3.7 ml. of 3.8M isethionic acid. Crystallization of the isethionate started after dilution with 400 ml. of absolute ether. The product was collected after several hours at room temperature, washed with absolute ether, and dissolved in 300 ml. of benzene. Water was removed azeotropically by distilling 200 ml. of benzene. The product was precipitated from the residual solution by dilution with 200 ml. of absolute ether; 5.8 g., m.p. 134.5°-136°. Recrystallization from 50 ml. of isopropyl alcohol - 200 ml. of absolute ether gave m.p. 135°-136.5°.

Workup

  1. dissolution(0.0132 mole), was dissolved in 20 ml
  2. customCrystallization of the isethionate
  3. customThe product was collected after several hours at room temperature
  4. washwashed with absolute ether
  5. dissolutiondissolved in 300 ml
  6. customWater was removed azeotropically
  7. distillationby distilling 200 ml
  8. customThe product was precipitated from the residual solution by dilution with 200 ml
  9. customRecrystallization from 50 ml
  10. customof absolute ether gave m.p. 135°-136.5°

Sources & evidence

ORD record
ord-7c7f1c93c1264e278f5845a0c9bb13ce
Source dataset
uspto-grants-1976_08
Patent number
US03978127

Reaction notes

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