Diethyl Ether → HCID 86615235, compound

HRID 2244363Notes

Reaction equation

HRID 2244363 reaction equation
[NH2:1]/[C:2](/[CH3:9])=[CH:3]\[C:4]([O:6][CH2:7][CH3:8])=[O:5].[CH:10]1([N:13]=[C:14]=[S:15])[CH2:12][CH2:11]1.C(OCC)C>CCCCCCC>[CH2:7]([O:6][C:4](=[O:5])[C:3]([C:14](=[S:15])[NH:13][CH:10]1[CH2:12][CH2:11]1)=[C:2]([NH2:1])[CH3:9])[CH3:8]

Participants

5

Reactant 3

HCID 3283Diethyl EtherHCID 92463Cyclopropyl isothiocyanateHCID 6437562-Butenoic acid, 3-amino-, ethyl ester, (2Z)-

Product 1

HCID 86615235HCID 86615235, compoundYield 45%

Reagents, catalysts & solvents 1

HCID 8900HeptaneSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 2.03 ml of ethyl 3-aminocrotonate (16 mmol) and 1.59 g of cyclopropyl iso-thiocyanate (16 mmol) was heated to 100° C. for 5 h. The reaction mixture was then cooled to 0° C. and diethyl ether (5 ml) and a small amount of heptane were added. An oily precipitate formed and after 5 min the solvents were decanted off. The remaining residue was triturated with a small amount of diethyl ether at 0° C. The precipitate was then filtered off and dried to give 1.64 g (45%) of 3-amino-2-cyclopropylthiocarbamoyl-but-2-enoic acid ethyl ester as a yellow solid. 1HNMR (DMSO-d6, 300 MHz): δ 0.60 (m, 2H), 0.76 (m, 2H), 1.11 (t, J=7.1 Hz, 3H), 1.90 (s, 3H), 3.28 (m, 1H), 3.97 (q, J=7.1 Hz, 2H), 7.24 (br s, 1H), 8.21 (br s, 1H), 9.79 (d, J=5.5 Hz, 1H).

Workup

  1. temperatureThe reaction mixture was then cooled to 0° C.
  2. customAn oily precipitate formed and after 5 min the solvents
  3. customwere decanted off
  4. customThe remaining residue was triturated with a small amount of diethyl ether at 0° C
  5. filtrationThe precipitate was then filtered off
  6. customdried

Sources & evidence

ORD record
ord-2d13bc9866f74e388635d3fe46168e23
Source dataset
uspto-grants-2010_03
Patent number
US07678818B2

Reaction notes

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