Acetic Acid → 1-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-one

HRID 220777

Reaction equation

HRID 220777 reaction equation
COC([C:5]1[CH2:11][CH2:10][N:9]([S:12]([C:15]2[CH:20]=[CH:19][C:18]([CH3:21])=[CH:17][CH:16]=2)(=[O:14])=[O:13])[C:8]2[CH:22]=[CH:23][CH:24]=[CH:25][C:7]=2[C:6]=1[OH:26])=O.C(OC(C1CCN(S(C2C=CC(C)=CC=2)(=O)=O)C2C=CC=CC=2C=1O)=O)C.C(O)(=O)C.Cl>C(O)C.O>[C:18]1([CH3:21])[CH:17]=[CH:16][C:15]([S:12]([N:9]2[CH2:10][CH2:11][CH2:5][C:6](=[O:26])[C:7]3[CH:25]=[CH:24][CH:23]=[CH:22][C:8]2=3)(=[O:14])=[O:13])=[CH:20][CH:19]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 54718720ethyl 5-hydroxy-1-tosyl-2,3-dihydro-1H-benzo[b]azepine-4-carboxylateHCID 575553885-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid methyl ester

Product 1

HCID 2668521-Tosyl-3,4-dihydro-1H-benzo[b]azepin-5(2H)-oneYield 60%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent2×

Procedure

A mixture of 5-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid methyl ester and 5-hydroxy-1-(toluene-4-sulfonyl)-2,3-dihydro-1H-benzo[b]azepine-4-carboxylic acid ethyl ester from Example E5.3 were heated at reflux in a mixture of ethanol (100 ml), acetic acid (300 ml), concentrated HCl (100 ml) and water (50 ml) for 18 h. The mixture was cooled to room temperature, diluted with water (800 ml) and extracted with chloroform. The combined organic ex-tracts were dried, filtered and reduced in vacuo. The residue was crystallised twice from methanol to yield the title compound (44 g, 60% over two steps).

Workup

  1. temperaturewere heated
  2. extractionextracted with chloroform
  3. customThe combined organic ex-tracts were dried
  4. filtrationfiltered
  5. customThe residue was crystallised twice from methanol

Sources & evidence

ORD record
ord-e70ace56b00e42cb9b06c565f7e98394
Source dataset
uspto-grants-2012_06
Patent number
US08202858B2

Linked notes

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