Toluene → HCID 9815601, compound

HRID 326534Notes

Reaction equation

HRID 326534 reaction equation
C(N(CC)CC)C.CC[S:10]([C:12]1[CH:24]=[CH:23][CH:22]=[CH:21][C:13]=1[C:14]([C:16]1[NH:17][CH:18]=[CH:19][CH:20]=1)=[O:15])=O.C1(C)C=CC=CC=1.C1N2C(SC3C=CC=CC=3C2=O)=CC=1>C(Cl)(Cl)Cl>[CH:20]1[CH:19]=[CH:18][N:17]2[C:16]=1[C:14](=[O:15])[C:13]1[CH:21]=[CH:22][CH:23]=[CH:24][C:12]=1[S:10]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 8471TriethylamineHCID 15006005HCID 15006005, compoundHCID 15272923HCID 15272923, compound

Product 1

HCID 9815601HCID 9815601, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Triethylamine (0.017 mL, 0.12 mmol, 0.1 eq), 2-(2-ethylsulfinyl) benzoyl pyrrole (0.3 g, 1.2 mmol), and toluene (15 mL) are combined and refluxed with stirring for 24 hours. After removal of volatiles in vacuo, a light brown oil is obtained which solidifies to a dark gold solid. Chromatography of the crude solid with a 1:1 ratio of CHCl3 to hexanes yields a product mix comprising 24 mg (0.12 mmol, 15 percent) of pyrrolo(2,1-b)-(1,3)benzothiazin-9-one, 114 mg (0.57 mmol, 69 percent) of pyrrolo(2,1-b)-(1,2)benzothiazin-10-one and 115 mg of light brown solid which proves by NMR to be a mixture of recovered starting material and 1H, 9H-(1)benzothiopyrano(3,2-b)pyrrol-9-one. By integration, the following approximate amounts for the above mixture are calculated: 93 mg (0.38 mmol) and 22 mg (0.11 mmol, 13 percent), respectively.

Workup

  1. temperaturerefluxed
  2. customAfter removal of volatiles in vacuo
  3. customa light brown oil is obtained which
  4. additiona mixture
  5. customof recovered

Sources & evidence

ORD record
ord-ad85b2940041424f9725061939dd5084
Source dataset
uspto-grants-1993_12
Patent number
US05270307

Reaction notes

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