Trifluoroacetic acid → HCID 138962835, compound

HRID 1872550Notes

Reaction equation

HRID 1872550 reaction equation
[C:1]([NH:9][C:10](=[N:13]C(OCCCC)=O)[S:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C1(OC)C=CC=CC=1.C(O)(C(F)(F)F)=O>>[C:1]([NH:9][C:10](=[NH:13])[S:11][CH3:12])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 6422Trifluoroacetic acidHCID 7519AnisoleHCID 57037267N-Benzoyl-N'-butyloxycarbonyl-S-methylisothiourea

Product 1

HCID 138962835HCID 138962835, compoundYield 128.7%

Procedure

To a mixture of 78b (160 mg, 0.54 mmol) and anisole (0.1 mL) was added TFA (1.0 mL). The resulting mixture was stirred for 30 min at room temperature, evaporated to dryness and put on vacuum line for 2 hours, and triturated with anhydrous Et2O to give 135 mg of 79b as a semi-solid. This crude product was used directly in the next step without further purification. 1HNMR (300 MHz, CD3OD): δ2.74 (3H, m); 7.55 (2H, t, J=7.8 Hz); 7.69 (1H, t, J=7.5 Hz); 8.02 (2H, d, J=7.5 Hz) ppm. IR (NaCl, film): 3226, 2936, 1695, 1680, 1540, 1188 cm-1.

Workup

  1. customevaporated to dryness
  2. waitput on vacuum line for 2 hours
  3. customtriturated with anhydrous Et2O

Sources & evidence

ORD record
ord-3ebaca66339644258fd85336defcb06d
Source dataset
uspto-grants-2000_08
Patent number
US06110925

Reaction notes

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