Sulfuryl chloride → 7-Chloro-2-phenothiazinecarbonitrile

HRID 704228Notes

Reaction equation

HRID 704228 reaction equation
[Cl-:1].[Al+3].[Cl-].[Cl-].S(Cl)(Cl)(=O)=O.[CH:10]1[C:23]2[NH:22][C:21]3[C:16](=[CH:17][CH:18]=[CH:19][CH:20]=3)[S:15][C:14]=2[CH:13]=[CH:12][C:11]=1[C:24]#[N:25]>ClCCCl>[Cl:1][C:18]1[CH:17]=[C:16]2[C:21](=[CH:20][CH:19]=1)[NH:22][C:23]1[CH:10]=[C:11]([C:24]#[N:25])[CH:12]=[CH:13][C:14]=1[S:15]2

Participants

5

Reactant 3

HCID 24648Sulfuryl chlorideHCID 98841Phenothiazine-2-carbonitrileHCID 6451240Aluminum(III) Chloride

Product 1

HCID 159253697-Chloro-2-phenothiazinecarbonitrileYield 7,143.1%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
25 °C

Procedure

Aluminium chloride (0.5 g) and sulphuryl chloride (39.7 cc) are added in the course of 4 hours to a solution, heated to 50° C., of 2-phenothiazinecarbonitrile (100 g) in 1,2-dichloroethane (3000 cc). The reaction mixture is brought to reflux for 2 hours, and then stirred for 48 hours at 25° C. The precipitate formed is filtered off, washed with 1,2-dichloroethane (2×200 cc) and then with ethyl ether (200 cc) and dried at 40° C. under reduced pressure (30 mm Hg; 4 kPa) to give 7-chloro-2-phenothiazinecarbonitrile (69.3 g) in the form of a yellow-green solid, m.p. 235° C.

Workup

  1. temperatureto reflux for 2 hours
  2. customThe precipitate formed
  3. filtrationis filtered off
  4. washwashed with 1,2-dichloroethane (2×200 cc)
  5. dry with materialwith ethyl ether (200 cc) and dried at 40° C. under reduced pressure (30 mm Hg; 4 kPa)

Sources & evidence

ORD record
ord-c9783dc49f314f3398cb9301c8f23c2a
Source dataset
uspto-grants-1991_01
Patent number
US04985419

Reaction notes

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