Iodine → 4H-Chromeno[4,3-d]thiazol-2-ylamine hydroiodide

HRID 2217341Notes

Reaction equation

HRID 2217341 reaction equation
[O:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4](=O)[CH2:3][CH2:2]1.[NH2:12][C:13]([NH2:15])=[S:14].[I:16]I>>[IH:16].[N:12]1[C:4]2[C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=3[O:1][CH2:2][C:3]=2[S:14][C:13]=1[NH2:15]

Participants

4

Reactant 3

HCID 807IodineHCID 68110ChromanoneHCID 2723790Thiourea

Product 1

HCID 497961204H-Chromeno[4,3-d]thiazol-2-ylamine hydroiodideYield 66.9%

Conditions

Temperature
95 °C

Procedure

A mixture of 4-chromanone (2.00 g; 13.5 mmol), thiourea (2.06 g; 27.0 mmol) and iodine (3.43 g; 13.5 mmol) were heated to 95° C. with stirring. After 4.5 hr., the mixture was allowed to cool to room temperature, triturated with methylene chloride, the solid material filtered off. The solid was further triturated with ethyl acetate, filtered and washed with ethyl acetate to provide 3.00 g of 4H-Chromeno[4,3-d]thiazol-2-ylamine hydroiodide 19 as an off white powder.

Workup

  1. temperatureto cool to room temperature
  2. customtriturated with methylene chloride
  3. filtrationthe solid material filtered off
  4. customThe solid was further triturated with ethyl acetate
  5. filtrationfiltered
  6. washwashed with ethyl acetate

Sources & evidence

ORD record
ord-aa7e8bd7dd65486099fd36fad06d7170
Source dataset
uspto-grants-2008_08
Patent number
US07407977B2

Reaction notes

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