Trifluoroacetic acid → HCID 58465956, compound

HRID 931567Notes

Reaction equation

HRID 931567 reaction equation
[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C:5]([CH:18]=[CH2:19])(O)[C:4]=2[CH:3]=1.[NH2:20][C:21]([NH2:23])=[S:22].C(O)(C(F)(F)F)=O>C(O)(=O)C>[Br:1][C:2]1[CH:15]=[CH:14][C:13]2[O:12][C:11]3[C:6](=[CH:7][C:8]([I:16])=[CH:9][CH:10]=3)[C:5]3([CH2:18][CH2:19][S:22][C:21]([NH2:23])=[N:20]3)[C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 2723790ThioureaHCID 57475651HCID 57475651, compound

Product 1

HCID 58465956HCID 58465956, compoundYield 63.7%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a solution of 2-bromo-7-iodo-9-vinyl-9H-xanthen-9-ol (0.50 g, 1.16 mmol) and thiourea (0.18 g, 2.33 mmol) in acetic acid (2.00 mL) was added TFA (4.00 mL). The reaction mixture was stirred at RT overnight. The reaction mixture was concentrated under reduced pressure and extracted with EtOAc, followed by a solvent mixture of CHCl3:i-PrOH (3:1). The combined organic layers were dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (10%-100% EtOAc/hexane) to provide 0.36 g of 2′-bromo-7′-iodo-5,6-dihydrospiro[[1,3]thiazine-4,9′-xanthen]-2-amine as a light yellow solid.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. extractionextracted with EtOAc
  3. additionfollowed by a solvent mixture of CHCl3:i-PrOH (3:1)
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by chromatography (10%-100% EtOAc/hexane)

Sources & evidence

ORD record
ord-099022cedb344b1bb33f28b878b13b59
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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