4-Toluenesulfonyl chloride → HCID 53810576, compound

HRID 2287041Notes

Reaction equation

HRID 2287041 reaction equation
[NH2:1][CH:2]([CH2:10][C:11]1[CH:16]=[CH:15][C:14]([O:17][CH3:18])=[CH:13][CH:12]=1)[C:3]([CH3:9])([CH3:8])[C:4]([O:6][CH3:7])=[O:5].C(N(CC)CC)C.[C:26]1([CH3:36])[CH:31]=[CH:30][C:29]([S:32](Cl)(=[O:34])=[O:33])=[CH:28][CH:27]=1>C(Cl)(Cl)Cl>[CH3:9][C:3]([CH3:8])([CH:2]([NH:1][S:32]([C:29]1[CH:30]=[CH:31][C:26]([CH3:36])=[CH:27][CH:28]=1)(=[O:34])=[O:33])[CH2:10][C:11]1[CH:12]=[CH:13][C:14]([O:17][CH3:18])=[CH:15][CH:16]=1)[C:4]([O:6][CH3:7])=[O:5]

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 8471TriethylamineHCID 23460866HCID 23460866, compound

Product 1

HCID 53810576HCID 53810576, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a solution of 251 g of methyl 3-amino-2,2-dimethyl-4-(p-methoxyphenyl)butyrate and 121 g of triethylamine in 750 ml of chloroform, there is added, with mechanical stirring and cooling with ice water, a solution of 210 g of p-toluenesulphonyl chloride in 500 ml of chloroform. After completion of the addition, which is carried out at such a rate that the temperature of the reaction mixture does not exceed 25° C., stirring is continued for 1.5 hours. Then the solution is washed with water, dilute hydrochloric acid and again with water, subsequently. After drying, the organic solvent is stripped off in vacuo. The residue is treated with ether, resulting in the crystallization of the title compound.

Workup

  1. additionAfter completion of the addition, which
  2. customdoes not exceed 25° C.
  3. stirringstirring
  4. washThen the solution is washed with water, dilute hydrochloric acid and again with water
  5. customAfter drying
  6. additionThe residue is treated with ether

Sources & evidence

ORD record
ord-afbf2d98918f4590bda6abec77df1668
Source dataset
uspto-grants-1981_05
Patent number
US04268673

Reaction notes

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