Acetic Acid → HCID 178469254, compound

HRID 1049963Notes

Reaction equation

HRID 1049963 reaction equation
[NH2:1]/[C:2](/[CH3:17])=[C:3](\[C:9](=[S:16])[NH:10][C:11](OCC)=[O:12])/[C:4]([O:6][CH2:7][CH3:8])=[O:5].C(O)(=O)C>C(N(CC)CC)C>[OH:12][C:11]1[N:10]=[C:9]([SH:16])[C:3]([C:4]([O:6][CH2:7][CH3:8])=[O:5])=[C:2]([CH3:17])[N:1]=1

Participants

4

Reactant 2

HCID 176Acetic AcidHCID 6042928HCID 6042928, compound

Product 1

HCID 178469254HCID 178469254, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Conditions

Temperature
70 °C

Procedure

(Z)-ethyl 3-amino-2-(ethoxycarbonylcarbamothioyl)but-2-enoate was dissolved in 30% aqueous triethyl amine and the reaction mixture stirred at 70° C. After 2 hours, the reaction mixture was cooled and neutralized with glacial acetic acid and the aqueous mixture extracted with EtOAc. The organic layer was washed with water, dried over Na2SO4 and concentrated under vacuum to give the desired product. 1H NMR (400 MHz, DMSO-d6): δ 12.54 (s, 1H), 11.85 (s, 1H), 4.21 (q, J=7.6 Hz, 2H), 2.03 (s, 3H), 1.24 (t. J=7.6 Hz, 3H); MS m/z 213.1 (M−1).

Workup

  1. temperaturethe reaction mixture was cooled
  2. extractionthe aqueous mixture extracted with EtOAc
  3. washThe organic layer was washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated under vacuum

Sources & evidence

ORD record
ord-9a7bc410288c4f408bf7e4f0b6c91980
Source dataset
uspto-grants-2016_07
Patent number
US09382277B2

Reaction notes

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