Thiophosgene → 2-Tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole

HRID 5787

Reaction equation

HRID 5787 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][CH:18]([CH3:21])[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-].[K+].[C:27](Cl)(Cl)=[S:28]>C(Cl)(Cl)Cl>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:27]=[S:28])[C:14]([N:15]3[CH2:20][CH2:19][CH:18]([CH3:21])[CH2:17][CH2:16]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 516893Potassium BicarbonateHCID 197941866-Amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole

Product 1

HCID 156103622-Tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

To a cooled mixture of 2.1 g of 6-amino-2-tert-butyl-5-(4-methylpiperidin-1-yl)benzothiazole and 2.8 g of potassium bicarbonate in 20 ml of chloroform is added dropwise 1.6 g of thiophosgene in 5 ml of chloroform under stirring. The stirring is continued for 2 hours maintaining the temperature at 0°-2° . The solid is filtered and the filtrate is evaporated. The solid thus obtained is dissolved in chloroform and filtered through a silica gel column. The filtrate is evaporated to give 2-tert-butyl-6-isothiocyanato-5-(4-methylpiperidin-1-yl)benzothiazole, melting at 54°-58°.

Workup

  1. temperaturemaintaining the temperature at 0°-2°
  2. filtrationThe solid is filtered
  3. customthe filtrate is evaporated
  4. customThe solid thus obtained
  5. filtrationfiltered through a silica gel column
  6. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-6cc07c4d63d84829877b5eb5f5957d9d
Source dataset
uspto-grants-1993_09
Patent number
US05246927

Linked notes

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