p-Toluenesulfonic acid monohydrate → 2-Fluorodibenzo[B,F][1,4]thiazepin-11(10H)-one

HRID 1692561Notes

Reaction equation

HRID 1692561 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8][C:9]1[CH:17]=[CH:16][C:15]([F:18])=[CH:14][C:10]=1[C:11](O)=[O:12].O.C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C(C)=CC=CC=1>[F:18][C:15]1[CH:16]=[CH:17][C:9]2[S:8][C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[NH:1][C:11](=[O:12])[C:10]=2[CH:14]=1

Participants

4

Reactant 2

HCID 521998p-Toluenesulfonic acid monohydrateHCID 580152732-(2-Aminophenylthio)-5-fluorobenzoic acid

Product 1

HCID 580152692-Fluorodibenzo[B,F][1,4]thiazepin-11(10H)-one

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

A suspension of 2-(2-aminophenylthio)-5-fluorobenzoic acid (64.57 mmol, 17.51 g) in 500 mL xylenes was treated with p-toluenesulfonic acid monohydrate (64.57 mmol, 12.2 g) and heated. Additional 200 mL xylene was added and heating was continued with azeotropic removal of water for 16 h. The resulting pink reaction mixture was cooled to the room temperature and added to 300 mL water. After stirring for 15 min the solid removed by filtration, washed with 3×100 mL water and dried in air for 4 h, and then under high vacuum for 20 h to obtain 2-fluorodibenzo[b,f][1,4]thiazepin-11(10H)-one as a off white solid (11.6 g, 73%); MS (M+1) 246; 1H NMR (300 MHz, DMSO-d6) δ ppm 7.16 (t, 1H) 7.24 (d, J=7.2 Hz, 1H) 7.29-7.42 (m, 2H) 7.47 (dd, J=9.3, 2.9 Hz, 1H) 7.52-7.71 (m, 2H) 10.47-11.20 (m, 1H), MS 081119 M+1 246 (0.72).

Workup

  1. temperatureheated
  2. temperatureheating
  3. customwas continued with azeotropic removal of water for 16 h
  4. additionadded to 300 mL water
  5. customremoved by filtration
  6. washwashed with 3×100 mL water
  7. customdried in air for 4 h

Sources & evidence

ORD record
ord-c7a61a84608849f9b351915f017f7942
Source dataset
uspto-grants-2012_04
Patent number
US08158618B2

Reaction notes

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