Sulfuric Acid → Dibenzothiazepinone

HRID 1350544Notes

Reaction equation

HRID 1350544 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[S:8]([C:11]1[CH:19]=[CH:18][CH:17]=[CH:16][C:12]=1[C:13](O)=[O:14])(=O)=O.S(=O)(=O)(O)O>C1(C)C(C)=CC=CC=1>[CH:16]1[C:12]2[C:13](=[O:14])[NH:1][C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=3[S:8][C:11]=2[CH:19]=[CH:18][CH:17]=1

Participants

4

Reactant 2

HCID 1118Sulfuric AcidHCID 21096911HCID 21096911, compound

Product 1

HCID 374829DibenzothiazepinoneYield 91.2%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Procedure

2-(2-aminophenylsulfuryl)benzoic acid (30 g, 0.122 mol) obtained in Example 5, sulfuric acid (0.15 g), and xylene (100 ml) were placed into a 0.5 L reactor, and then refluxed at 145–150° C. for six hours. The resultants were cooled to room temperature, after which the produced solid was filtered and washed with methanol. The solid was dried under reduced pressure, to give 10H-dibenzo[b,f][1,4]thiazepin-11-one (25.3 g), as the yield of 91%.

Workup

  1. temperaturerefluxed at 145–150° C. for six hours
  2. filtrationafter which the produced solid was filtered
  3. washwashed with methanol
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-349eda178c724c45b3eb1dc53b541008
Source dataset
uspto-grants-2007_05
Patent number
US07214793B2

Reaction notes

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