Thiophosgene → HCID 20192956, compound

HRID 2118755Notes

Reaction equation

HRID 2118755 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:17][CH2:16]2)=[CH:13][C:5]2[N:6]=[C:7]([C:9]([CH3:12])([CH3:11])[CH3:10])[S:8][C:4]=2[CH:3]=1.C(=O)(O)[O-].[Na+].[C:30](Cl)(Cl)=[S:31]>C(Cl)(Cl)Cl>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:30]=[S:31])[C:14]([N:15]3[CH2:16][CH2:17][N:18]([S:21]([CH3:24])(=[O:23])=[O:22])[CH2:19][CH2:20]3)=[CH:13][C:5]=2[N:6]=1)([CH3:11])([CH3:12])[CH3:10]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 20192950HCID 20192950, compound

Product 1

HCID 20192956HCID 20192956, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

A mixture of 1 g of 6-amino-2-tert-butyl-5-[4-methanesulphonylpiperazin-1-yl]benzothiazole and 500 g of sodium bicarbonate in 100 ml of chloroform is cooled in an ice-bath and 2 ml of thiophosgene in 10 ml of chloroform is added to it under stirring. The mixture is stirred over-night at ambient temperature. After filtering off the solid the filtrate is evaporated and the residue is subjected to silica gel column chromatography. Elution with 1% methanol in chloroform gives 2-tert-butyl-6-isothiocyanato-5-[4-methanesulphonylpiperazin-1-yl]benzothiazole melting at 128°-130°.

Workup

  1. temperatureis cooled in an ice-bath
  2. stirringThe mixture is stirred over-night at ambient temperature
  3. filtrationAfter filtering off the solid the filtrate
  4. customis evaporated
  5. washElution with 1% methanol in chloroform

Sources & evidence

ORD record
ord-40be1db09f6547619bdf95c995083446
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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