Thiophosgene → HCID 20192945, compound

HRID 2118753Notes

Reaction equation

HRID 2118753 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[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:29](Cl)(Cl)=[S:30]>C(Cl)(Cl)Cl>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:29]=[S:30])[C:14]([N:15]3[CH2:20][CH2:19][N:18]([C:21](=[O:23])[CH3:22])[CH2:17][CH2:16]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:10])[CH3:11]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 20192928HCID 20192928, compound

Product 1

HCID 20192945HCID 20192945, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

A mixture of 2 g of 6-amino-2-tert-butyl-5-[4-acetylpiperazin-1-yl]benzothiazole and 1.5 g of sodium bicarbonate in 150 ml of chloroform is cooled to 0° and 4 ml of thiophosgene is added dropwise and stirred at ambient temperature overnight. The solid is filtered off and the filtrate is evaporated under reduced pressure. The oil so obtained is applied on a silica gel column and eluted with 1% methanol in chloroform to yield 2-tert-butyl-6-isothiocyanato-5-[4-acetylpiperazin-1-yl]benzothiazole, melting at 100°-102°.

Workup

  1. temperatureis cooled to 0°
  2. filtrationThe solid is filtered off
  3. customthe filtrate is evaporated under reduced pressure
  4. customThe oil so obtained
  5. washeluted with 1% methanol in chloroform

Sources & evidence

ORD record
ord-b0bff6f94f124e229af9a301d4c951a2
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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