Thiophosgene → HCID 20192930, compound

HRID 2118745Notes

Reaction equation

HRID 2118745 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][O:18][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:26](Cl)(Cl)=[S:27]>C(Cl)(Cl)Cl.CCCCCC>[C:9]([C:7]1[S:8][C:4]2[CH:3]=[C:2]([N:1]=[C:26]=[S:27])[C:14]([N:15]3[CH2:16][CH2:17][O:18][CH2:19][CH2:20]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

6

Reactant 3

HCID 10040ThiophosgeneHCID 516892Sodium BicarbonateHCID 20192925HCID 20192925, compound

Product 1

HCID 20192930HCID 20192930, compound

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 8058HexaneSolvent

Procedure

To a cooled mixture of 143 g of 6-amino-2-tert-butyl-5-morpholinobenzothiazole and 168 g of sodium bicarbonate in 200 ml of CHCl3 is added 75 g of thiophosgene under stirring. The stirring is continued at ambient temperature for 10 hours. The solide are filtered off and the filtrate is evaporated. The solid thus obtained is dissolved in hexane and filtered through a silica gel column. The filtrate is evaporated to give 2-tert-butyl-6-isothiocyanato-5-[morpholin-4-yl]benzothiazole melting at 141°-143°.

Workup

  1. filtrationThe solide are filtered off
  2. customthe filtrate is evaporated
  3. customThe solid thus obtained
  4. filtrationfiltered through a silica gel column
  5. customThe filtrate is evaporated

Sources & evidence

ORD record
ord-ae089819909845b2ba3f324253b40af7
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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