Thiophosgene → HCID 20192921, compound

HRID 2118748Notes

Reaction equation

HRID 2118748 reaction equation
[NH2:1][C:2]1[C:14]([N:15]2[CH2:20][CH2:19][S: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-].[K+].[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[CH2:16][CH2:17][S:18][CH2:19][CH2:20]3)=[CH:13][C:5]=2[N:6]=1)([CH3:12])([CH3:11])[CH3:10]

Participants

5

Reactant 3

HCID 10040ThiophosgeneHCID 11430Potassium CarbonateHCID 20192920HCID 20192920, compound

Product 1

HCID 20192921HCID 20192921, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a mixture of 2 g of 6-amino-2-tert-butyl-5-[thiomorpholin-4-yl]benzothiazole and 2 g of anhydrous potassium carbonate in 150 ml of chloroform at 0° is added 0.6 ml of thiophosgene in 5 ml chloroform, under stirring. After 4 hours of stirring at ambient temperature the mixture is filtered. The filtrate is evaporated to a solid which is purified by silica gel column chromatography. The column is eluted with hexane/methylenechloride (1:1) to give 2-tert-butyl-6-isothiocyanato-5-[thiomorpholin-4-yl]benzothiazole, melting at 155°-159°.

Workup

  1. stirringAfter 4 hours of stirring at ambient temperature the mixture
  2. filtrationis filtered
  3. customThe filtrate is evaporated to a solid which
  4. customis purified by silica gel column chromatography
  5. washThe column is eluted with hexane/methylenechloride (1:1)

Sources & evidence

ORD record
ord-e9f8b1b28cc44f8aac13a98fdda19f6f
Source dataset
uspto-grants-1987_07
Patent number
US04680301

Reaction notes

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