Thiophosgene → 2-Tert-butyl-6-isocyanato-5-[4-methyl-piperazin-1-yl]benzothiazole

HRID 2118742

Reaction equation

HRID 2118742 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][N: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:22](=O)(O)[O-:23].[Na+].C(Cl)(Cl)=S.[OH-].[Na+]>C(Cl)(Cl)Cl.O>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:22]=[O:23])[C:14]([N:15]3[CH2:20][CH2:19][N:18]([CH3:21])[CH2:17][CH2:16]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

7

Reactant 4

HCID 10040ThiophosgeneHCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 197941766-Amino-2-tert-butyl-5-(4-methylpiperazin-1-yl)benzothiazole

Product 1

HCID 201929472-Tert-butyl-6-isocyanato-5-[4-methyl-piperazin-1-yl]benzothiazole

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6212ChloroformSolvent

Procedure

To a stirred mixture of 75 g of 6-amino-2-tert-butyl-5-(4-methylpiperazin-1-yl)benzothiazole and 29 g of sodium bicarbonate in 1100 ml of chloroform at 0° is added 41 g of thiophosgene and the mixture stirred at 10° for 4 hours. After filtering off the solid, the solution is evaporated to get an yellow solid which is dissolved in water and the pH of the solution is brought to 7 by the addition of dilute sodium hydroxide. The solid separated is extracted with hexane and filtered through 150 g of neutral alumina to give 2-tert-butyl-6-isocyanato-5-[4-methyl-piperazin-1-yl]benzothiazole melting at 124°-126°.

Workup

  1. filtrationAfter filtering off the solid
  2. customthe solution is evaporated
  3. customto get an yellow solid which
  4. customThe solid separated
  5. extractionis extracted with hexane
  6. filtrationfiltered through 150 g of neutral alumina

Sources & evidence

ORD record
ord-d2d22f0b5f2142f4b68d026ed0663809
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Linked notes

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