p-Toluenesulfonic acid monohydrate → p-Toluenesulfonic acid

HRID 1833430Notes

Reaction equation

HRID 1833430 reaction equation
O.[C:2]1([CH3:12])[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1>CC(C)=O>[CH3:12][C:2]1[CH:7]=[CH:6][C:5]([S:8]([OH:11])(=[O:10])=[O:9])=[CH:4][CH:3]=1

Participants

3

Reactant 1

HCID 521998p-Toluenesulfonic acid monohydrate

Product 1

HCID 6101p-Toluenesulfonic acidYield 83%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
25 °C

Procedure

To a stirred slurry of 6-triphenylmethylamino-2,2-dimethyl-3-(O,O-dimethylphosphono)penam, 487 mg. (0.001 mole), in 10 ml. of dry acetone is added 190 mg. (0.001 mole) of p-toluenesulfonic acid monohydrate at 25° C. The solids dissolve slowly, giving a clear solution. After stirring at 25° C. for 15 minutes the product starts to precipitate. The stirring is continued for a further 45 minutes after the product starts to appear. The first crop is then filtered off, washed with acetone, and dried to afford the title compound as the p-toluenesulfonate salt. 1H-nmr (DMSO-d6) ppm (δ): 1.65 (s,3,CH3), 1.70 (s,3,CH3), 2.32 (s,3,CH3), 3.77 (d,J = 11,6,OCH3), 4.11 (d,J = 11, 1,C-3), 5.1 (m,l)- and 5.45 (d,J = 4,1)- C-5 and C-6 protons, 7.3 (q,4,aromatic protons). The yield is 83% of theory, M.P. 149°-151° C.

Workup

  1. customat 25° C
  2. dissolutionThe solids dissolve slowly
  3. customgiving a clear solution
  4. customto precipitate
  5. waitThe stirring is continued for a further 45 minutes
  6. filtrationThe first crop is then filtered off
  7. washwashed with acetone
  8. customdried

Sources & evidence

ORD record
ord-dbadaf839e864e8f8aaf1c8bd4ba2668
Source dataset
uspto-grants-1978_01
Patent number
US04066657

Reaction notes

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