m-Chloroperbenzoic acid → HCID 15165517, compound

HRID 2255456Notes

Reaction equation

HRID 2255456 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[C:5]([N:7]=[C:8]1[N:12]([CH2:13][CH2:14][C:15](=[S:17](=[O:19])=[O:18])C)[C:11]2[CH:20]=[CH:21][C:22]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:23][C:10]=2[S:9]1)=[O:6].Cl[C:33]1C=CC=C(C(OO)=O)C=1.N=C1N(CCCSC)C2C=CC(OC(F)(F)F)=CC=2S1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([CH:29]=[CH:30][CH:31]=1)[C:5]([N:7]=[C:8]1[N:12]([CH2:13][CH2:14][CH2:15][S:17]([CH3:33])(=[O:19])=[O:18])[C:11]2[CH:20]=[CH:21][C:22]([O:24][C:25]([F:28])([F:27])[F:26])=[CH:23][C:10]=2[S:9]1)=[O:6]

Participants

5

Reactant 3

HCID 70297m-Chloroperbenzoic acidHCID 105438302(3H)-Benzothiazolimine, 3-[3-(methylthio)propyl]-6-(trifluoromethoxy)-HCID 86747166HCID 86747166, compound

Product 1

HCID 15165517HCID 15165517, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

2-(3-Chlorobenzoylimino)-3-(3-methyl-sulphonylpropyl)-6-trifluoromethoxybenzothiazoline may be prepared in the following way: 75% m-chloro-perbenzoic acid (5.2 g) is added in the course of about 10 minutes, to 2-imino-3-(3-methylthiopropyl)-6-trifluoromethoxybenzothiazoline (3.9 g) in solution in dichloromethane (100 cc) stirred at a temperature close to 20° C. The reaction mixture is brought to the boil for 18 hours. After cooling to a temperature close to 20° C., the precipitate is filtered off and washed with dichloromethane (50 cc) and the filtrate is concentrated to dryness under reduced pressure after washing with 1N sodium hydroxide solution. The oil obtained is crystallised from ethyl acetate. 2-(3-Chlorobenzoylimino)-3-(3-methylsulphonylpropyl)-6-trifluoromethoxybenzothiazoline (0.6 g) melting at 188° C. is obtained.

Workup

  1. customclose to 20° C
  2. temperatureAfter cooling to a temperature
  3. customclose to 20° C.
  4. filtrationthe precipitate is filtered off
  5. washwashed with dichloromethane (50 cc)
  6. concentrationthe filtrate is concentrated to dryness under reduced pressure
  7. washafter washing with 1N sodium hydroxide solution
  8. customThe oil obtained
  9. customis crystallised from ethyl acetate

Sources & evidence

ORD record
ord-a5209cc5b8d843d1aa5bafde76a3176a
Source dataset
uspto-grants-1993_08
Patent number
US05240948

Reaction notes

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