Methanesulfonyl chloride → HCID 178457587, compound

HRID 1030219Notes

Reaction equation

HRID 1030219 reaction equation
[C:1]([N:3]=[C:4]([NH:7][C@@H:8]1[C:13]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH3:21])([CH3:20])[C@H:9]1[OH:22])[CH2:5][CH3:6])#[N:2].[S:23](Cl)([CH3:26])(=[O:25])=[O:24]>N1C=CC=CC=1>[C:1]([N:3]=[C:4]([NH:7][C@@H:8]1[C:13]2[CH:14]=[C:15]([C:18]#[N:19])[CH:16]=[CH:17][C:12]=2[O:11][C:10]([CH3:21])([CH3:20])[C@H:9]1[O:22][S:23]([CH3:26])(=[O:25])=[O:24])[CH2:5][CH3:6])#[N:2]

Participants

4

Reactant 2

HCID 31297Methanesulfonyl chlorideHCID 178457586HCID 178457586, compound

Product 1

HCID 178457587HCID 178457587, compoundYield 79.8%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of trans-4-[N-[1-(cyanoimino)propyl]amino]-3,4-dihydro-2,2-dimethyl-3-hydroxy-2H-1-benzopyran-6-carbonitrile (1.49 g) in dry pyridine (7.5 ml) was added dropwise mesyl chloride (0.77 g) under ice-water cooling. The resulting mixture was stirred overnight at room temperature and concentrated under reduced pressure. The residue was dissolved in a mixture of ethyl acetate and washed with 5% hydrochloric acid (twice), aqueous sodium bicarbonate and brine, successively. The organic layer was dried over anhydrous magnesium sulfate and evaporated in vacuo. The residue was recrystallized from ethanol to give trans-4-[N-[1-(cyanoimino)propyl]amino]-3,4-dihydro-2,2-dimethyl-3-mesyloxy-2H-1-benzopyran-6-carbonitrile (1.50 g).

Workup

  1. concentrationconcentrated under reduced pressure
  2. dissolutionThe residue was dissolved in a mixture of ethyl acetate
  3. washwashed with 5% hydrochloric acid (twice), aqueous sodium bicarbonate and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated in vacuo
  6. customThe residue was recrystallized from ethanol

Sources & evidence

ORD record
ord-297d456a28554bf79bcaa48ce3d16f7b
Source dataset
uspto-grants-1992_04
Patent number
US05104890

Reaction notes

Loading…