p-Toluenesulfonic acid → HCID 23452432, compound

HRID 1277919Notes

Reaction equation

HRID 1277919 reaction equation
[O:1]1[C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[CH2:4][C:3](=O)[CH2:2]1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH2:29]>C1(C)C=CC=CC=1>[CH3:25][N:26]([CH3:30])[CH2:27][CH2:28][NH:29][C:3]1[CH2:2][O:1][C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][C:6]=2[C:5](=[O:12])[CH:4]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 66053N,N-DimethylethylenediamineHCID 3196771-Benzoxepin-3,5(2H,4H)-dione

Product 1

HCID 23452432HCID 23452432, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A solution of 88 g (0.5 mole) 2,3,4,5-tetrahydro-1-benzoxepin-3,5-dione and a spatula tip of p-toluene sulfonic acid in 750 ml toluene are mixed while stirring with 44 g (0.5 mole) N,N-dimethylethylenediamine and subsequently stirred to the end of the reaction at room temperature. After concentration of the solution, a product is obtained by filtering off the solution under suction and subsequently recrystallizing from benzene/ligroin. 108 g (88% of the theoretical yield) of 3-(β-dimethylaminoethylamino)-1-benzoxepin-5(2H)-one are obtained. The melting point of this derivative is 100 to 101° C.

Workup

  1. customAfter concentration of the solution, a product is obtained
  2. filtrationby filtering off the solution under suction
  3. customsubsequently recrystallizing from benzene/ligroin

Sources & evidence

ORD record
ord-73326f1285fd4f1fa3a91bdea6a8fb0c
Source dataset
uspto-grants-1981_07
Patent number
US04279905

Reaction notes

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