Methanol → HCID 20192931, compound

HRID 2118751Notes

Reaction equation

HRID 2118751 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][N:18]([C:21]([O:23][CH2:24][CH3:25])=[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:31](Cl)(Cl)=[S:32].CO>C(Cl)(Cl)Cl>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:31]=[S:32])[C:14]([N:15]3[CH2:16][CH2:17][N:18]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[CH2:19][CH2:20]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 887MethanolHCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 20192924HCID 20192924, compound

Product 1

HCID 20192931HCID 20192931, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent3×

Procedure

A mixture of 2 g of 6-amino-2-tert-butyl-5[4-carbethoxypiperazin-1-yl]benzothiazole and 2 g of sodium bicarbonate in 200 ml of chloroform is cooled in an ice bath and 4 ml of thiophosgene in 10 ml of chloroform is added and the mixture is stirred at ambient temperature for 2 hours. The solid is filtered off and the filtrate is evaporated to give an oil which is applied on a silica gel column with 1% methanol in chloroform to yield 2-tert-butyl-5-[4-carbethoxypiperazin-1-yl]-6-isothiocyanato-benzothiazole, melting at 131°-134°.

Workup

  1. temperatureis cooled in an ice bath
  2. filtrationThe solid is filtered off
  3. customthe filtrate is evaporated
  4. customto give an oil which

Sources & evidence

ORD record
ord-e13f3f8168e347cbb887986542336ba9
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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