Methanesulfonyl chloride → HCID 20253656, compound

HRID 638214Notes

Reaction equation

HRID 638214 reaction equation
O.Cl.Cl.[NH2:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:21])[NH:16]3)[CH:8]=[CH:9][CH:10]=1.[CH3:22][S:23]([Cl:26])(=[O:25])=[O:24]>N1C=CC=CC=1>[ClH:26].[CH3:22][S:23]([NH:4][C:5]1[CH:6]=[C:7]([C:11]2[N:20]=[CH:19][CH:18]=[C:17]3[C:12]=2[CH:13]=[CH:14][C:15](=[O:21])[NH:16]3)[CH:8]=[CH:9][CH:10]=1)(=[O:25])=[O:24]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 20253638HCID 20253638, compound

Product 1

HCID 20253656HCID 20253656, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a mixture containing 6.57 g of 5-(3-aminophenyl)-1,6-naphthyridin-2(1H)-one dihydrochloride monohydrate and 64 ml of pyridine was added dropwise with stirring 2.9 ml of methanesulfonyl chloride and the reaction mixture was stirred for about 30 minutes. The reaction mixture was concentrated on a rotary evaporator and to the residual oily material was added water whereupon a solid separated and then dissolved. To the solution was added about 10 ml of acetic acid and the mixture allowed to stand overnight. The solution was concentrated on a rotary evaporator and to the residue was added ethanol whereupon on standing crystallization resulted. The crystalline material was collected, washed with ethanol and dried in a vacuum oven at 90° C. to yield 6.0 g of 5-(3-methanesulfonylaminophenyl)-1,6-naphthyridin-2(1H)-one monohydrochloride, m.p. 258° C. with decomposition.

Workup

  1. additionwas added dropwise
  2. concentrationThe reaction mixture was concentrated on a rotary evaporator and to the residual oily material
  3. additionwas added water whereupon a solid
  4. customseparated
  5. dissolutiondissolved
  6. additionTo the solution was added about 10 ml of acetic acid
  7. waitto stand overnight
  8. concentrationThe solution was concentrated on a rotary evaporator and to the residue
  9. additionwas added ethanol whereupon
  10. customcrystallization
  11. customresulted
  12. customThe crystalline material was collected
  13. washwashed with ethanol
  14. customdried in a vacuum oven at 90° C.

Sources & evidence

ORD record
ord-72cbb3c8e046440cb2418cb454ffdbb9
Source dataset
uspto-grants-1985_12
Patent number
US04560691

Reaction notes

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