p-Toluenesulfonic acid monohydrate → HCID 54372552, compound

HRID 974332Notes

Reaction equation

HRID 974332 reaction equation
[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH2:13][CH:14]([C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[O:24][CH3:25])O)[CH2:8][CH2:9][C:10]=2[N:11]=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[NH2:1][C:2]1[S:3][C:4]2[CH2:5][CH2:6][N:7]([CH2:12][CH:13]=[CH:14][C:16]3[CH:21]=[CH:20][C:19]([O:22][CH3:23])=[CH:18][C:17]=3[O:24][CH3:25])[CH2:8][CH2:9][C:10]=2[N:11]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 19985774HCID 19985774, compound

Product 1

HCID 54372552HCID 54372552, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

0.45 g (1.2 mmol) of 2-amino-6-(3-(2,4-dimethoxy-phenyl)-3-hydroxy-1-propyl)-4,5,7,8-tetrahydro-6H-thiazolo[5,4-d]azepine are stirred in 35 ml of anhydrous toluene together with 0.47 g (2.7 mmol) of p-toluenesulphonic acid hydrate and 7 g of molecular sieve (4Å) in a bath at 40° C. After one hour, a further 5 g of molecular sieve are added and after a total of 2 hours a further 2.5 g of molecular sieve are added. After a total of 3 hours at 40° C. the mixture is filtered through a glass frit coated with Celite and the filter cake is washed out several times with chloroform. The toluene and chloroform solutions are extracted with semi-concentrated ammonia and with water, then dried and filtered and evaporated down in vacuo. The combined evaporation residues are purified by column chromatography on silica gel (toluene/ethyl acetate/methanol/conc. ammonia=4:3:1:0.5). Yield: 43 mg (10% of theory), Melting point: 95°-100° C. (ether).

Workup

  1. additiona further 5 g of molecular sieve are added
  2. additionafter a total of 2 hours a further 2.5 g of molecular sieve are added
  3. filtrationAfter a total of 3 hours at 40° C. the mixture is filtered through a glass frit
  4. washthe filter cake is washed out several times with chloroform
  5. extractionThe toluene and chloroform solutions are extracted with semi-concentrated ammonia and with water
  6. customdried
  7. filtrationfiltered
  8. customevaporated down in vacuo
  9. customThe combined evaporation residues
  10. customare purified by column chromatography on silica gel (toluene/ethyl acetate/methanol/conc. ammonia=4:3:1:0.5)

Sources & evidence

ORD record
ord-baa2cacaa41e4d6fb5d7fec0dee42209
Source dataset
uspto-grants-1991_11
Patent number
US05068325

Reaction notes

Loading…