Dimethylsulphamoyl chloride → HCID 15463643, compound

HRID 1106450Notes

Reaction equation

HRID 1106450 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[N:9]([CH:10]=1)[C:8](=[O:11])[C:7]1[C:12]([OH:20])=[C:13]([CH2:17][CH2:18][CH3:19])[C:14]([OH:16])=[CH:15][C:6]=1[O:5]2.[CH3:21][N:22]([CH3:27])[S:23](Cl)(=[O:25])=[O:24]>C1(C)C=CC=CC=1.CN(C)C1C=CN=CC=1.C(OCC)(=O)C>[CH3:21][N:22]([CH3:27])[S:23](=[O:25])(=[O:24])[O:16][C:14]1[C:13]([CH2:17][CH2:18][CH3:19])=[C:12]([OH:20])[C:7]2[C:8](=[O:11])[N:9]3[CH:10]=[C:2]([Cl:1])[CH:3]=[C:4]3[O:5][C:6]=2[CH:15]=1

Participants

6

Reactant 2

HCID 83372Dimethylsulphamoyl chlorideHCID 9796118HCID 9796118, compound

Product 1

HCID 15463643HCID 15463643, compoundYield 71.1%

Reagents, catalysts & solvents 3

HCID 142844-(Dimethylamino)pyridineCatalystHCID 1140TolueneSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
85 °C

Procedure

To 80 mg (0.27 mmol) of 2-chloro-6,8-dihydroxy-7-propyl-9H-pyrrolo [2,1-b][1,3]benzoxazin-9-one in 3 mL of toluene was added 0.3 mL (2.77 mmol) of dimethylsulfamylchloride and 0.066 g (0.54 mmol) of 4-dimethylaminopyridine (DMAP). The mixture was heated to 85° C. for 2 hr. It was cooled, diluted with ethyl acetate and extracted two times with 1N HCl. The organic layer was dried (Na2SO4) and concentrated. The residue was purified by preparative TLC (hexane: CH2Cl2 ; 1:1) to give 77 mg of the title compound mp 159-160° C.

Workup

  1. temperatureIt was cooled
  2. extractionextracted two times with 1N HCl
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. concentrationconcentrated
  5. customThe residue was purified by preparative TLC (hexane: CH2Cl2 ; 1:1)

Sources & evidence

ORD record
ord-e0b6d01317b4456ab57ca65817ca1d78
Source dataset
uspto-grants-2000_05
Patent number
US06057315

Reaction notes

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