Trifluoroacetic acid → Thiomorpholine-4-carboximidamide

HRID 72805Notes

Reaction equation

HRID 72805 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15](=[N:22]C(OC(C)(C)C)=O)[N:16]1[CH2:21][CH2:20][S:19][CH2:18][CH2:17]1)(C)(C)C>C(Cl)Cl.O>[N:16]1([C:15]([NH2:22])=[NH:14])[CH2:21][CH2:20][S:19][CH2:18][CH2:17]1

Participants

5

Reactant 2

HCID 6422Trifluoroacetic acidHCID 67369775(tert-Butoxycarbonylimino-thiomorpholin-4-yl-methyl)-carbamic acid tert-butyl ester

Product 1

HCID 2774443Thiomorpholine-4-carboximidamide

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (50 mL, 0.073 mol) was added dropwise to a stirred mixture of (tert-Butoxycarbonylimino-thiomorpholin-4-yl-methyl)-carbamic acid tert-butyl ester (21 g, 0.0723 mol) in DCM (200 mL) and water (10 mL). After 3 days at rt, the solvent was evaporated and re-evaporated with 2-propanol. The resulting semi-solid was triturated with 10% 2-propanol/Et2O. The solid was filtered off and was washed with 10% 2-propanol/Et2O and then with Et2O. The product was dried in vacuo over phosphoric oxide, to give 15.72 g as a white solid.

Workup

  1. customthe solvent was evaporated
  2. customre-evaporated with 2-propanol
  3. customThe resulting semi-solid was triturated with 10% 2-propanol/Et2O
  4. filtrationThe solid was filtered off
  5. washwas washed with 10% 2-propanol/Et2O
  6. dry with materialThe product was dried in vacuo over phosphoric oxide
  7. customto give 15.72 g as a white solid

Sources & evidence

ORD record
ord-5996e178d1174d029e02456f620ec262
Source dataset
uspto-grants-2014_09
Patent number
US08829011B2

Reaction notes

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