Trifluoroacetic acid → 3,4-Dihydro-2H-1-benzothiopyran-8-amine

HRID 1739793Notes

Reaction equation

HRID 1739793 reaction equation
C(OC([NH:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[S:17][CH2:16][CH2:15][CH2:14]2)=O)(C)(C)C.FC(F)(F)C(O)=O>ClCCl>[NH2:8][C:9]1[CH:10]=[CH:11][CH:12]=[C:13]2[C:18]=1[S:17][CH2:16][CH2:15][CH2:14]2

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 21837517HCID 21837517, compound

Product 1

HCID 133713753,4-Dihydro-2H-1-benzothiopyran-8-amineYield 71.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

10 g (37.7 mmol) of the compound obtained in Step 1 above in 50 ml of dichloromethane are mixed with 50 ml of trifluoroacetic acid, and the mixture is stirred for 30 minutes at room temperature and then evaporated to dryness. The residue is taken up in ether and the solid obtained is filtered off and treated with N sodium hydroxide solution. The aqueous phase is extracted with ether and the ethereal phases are combined, dried over magnesium sulphate and concentrated to yield 4.48 g of the desired product (theory: 6.2 g).

Workup

  1. customevaporated to dryness
  2. customthe solid obtained
  3. filtrationis filtered off
  4. additiontreated with N sodium hydroxide solution
  5. extractionThe aqueous phase is extracted with ether
  6. dry with materialdried over magnesium sulphate
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-ad4b85f79fcb43cc906b085571ce6700
Source dataset
uspto-grants-1999_10
Patent number
US05968954

Reaction notes

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