Methanesulfonic Acid → HCID 58424601, compound

HRID 2096625Notes

Reaction equation

HRID 2096625 reaction equation
Cl.[C:2]([S:5][CH2:6][CH:7]=[C:8]1[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([Br:18])[CH:16]=2)[O:11][CH:10]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH2:9]1)(=[NH:4])[NH2:3].NC(N)=S.CS(O)(=O)=O>C(O)(C(F)(F)F)=O>[Br:18][C:15]1[CH:16]=[C:17]2[C:8]3([CH2:7][CH2:6][S:5][C:2]([NH2:3])=[N:4]3)[CH2:9][CH:10]([C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[O:11][C:12]2=[CH:13][CH:14]=1

Participants

5

Reactant 3

HCID 6395Methanesulfonic AcidHCID 2723790ThioureaHCID 67173773HCID 67173773, compound

Product 1

HCID 58424601HCID 58424601, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

The above mixture of 2-(6-bromo-2-phenylchroman-4-ylidene)ethyl carbamimidothioate HCl salt and thiourea is dissolved in TFA (4 mL) containing MeSO3H (0.4 mL) and stirred at rt for 1 h. The solvent is removed under reduced pressure. The residue is dissolved in ethyl acetate and washed with sat NaHCO3. The separated aqueous phase is extracted with ethyl acetate once and the combined organic phases are washed with brine, and dried over Na2SO4, and filtered. The filtrate is concentrated to give crude 6-bromo-2-phenyl-5′,6′-dihydrospiro[chroman-4,4′-[1,3]thiazin]-2′-amine, which is used for next step without further purification.

Workup

  1. customThe solvent is removed under reduced pressure
  2. dissolutionThe residue is dissolved in ethyl acetate
  3. washwashed
  4. extractionThe separated aqueous phase is extracted with ethyl acetate once
  5. washthe combined organic phases are washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-c857bbe58f9e48b3b7742934dc264201
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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