Sodium Cyanide → HCID 13784629, compound

HRID 235643Notes

Reaction equation

HRID 235643 reaction equation
Br[CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6]1.[C-:16]#[N:17].[Na+]>CS(C)=O.O>[C:16]([CH2:2][CH2:3][CH2:4][CH:5]1[C:10](=[O:11])[NH:9][C:8]2[CH:12]=[CH:13][CH:14]=[CH:15][C:7]=2[S:6]1)#[N:17]

Participants

5

Reactant 2

HCID 8929Sodium CyanideHCID 137846142-(3-Bromopropyl)-2H-1,4-benzothiazin-3(4H)-one

Product 1

HCID 13784629HCID 13784629, compoundYield 66.8%

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 962WaterSolvent

Procedure

To a solution of 2.86 g of 2-(3-bromopropyl)-2H-1,4-benzothiazin-3(4H)-one in 10 ml of dimethyl sulfoxide was added 0.54 g of sodium cyanide. The mixture was stirred at room temperature for 3 hours and diluted with water. The resulting crystals were collected by filtration and washed with water. Recrystallization from methanol gave 1.55 g (66.7%) of 2-(3-cyanopropyl)-2H-1,4-benzothiazin-3(4H)-one as prisms, m.p. 107°-108° C.

Workup

  1. filtrationThe resulting crystals were collected by filtration
  2. washwashed with water
  3. customRecrystallization from methanol

Sources & evidence

ORD record
ord-d76a607017b3410eb915377e77f71981
Source dataset
uspto-grants-1987_02
Patent number
US04640916

Reaction notes

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