Ethyl iodoacetate → Ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylate

HRID 572610Notes

Reaction equation

HRID 572610 reaction equation
N1([CH:7]=[C:8]([C:11]([N:13]2[CH2:18][CH2:17][O:16][CH2:15][CH2:14]2)=[S:12])[C:9]#[N:10])CCOCC1.I[CH2:20][C:21]([O:23][CH2:24][CH3:25])=[O:22].CCN(C(C)C)C(C)C>C(#N)C>[C:9]([C:8]1[CH:7]=[C:20]([C:21]([O:23][CH2:24][CH3:25])=[O:22])[S:12][C:11]=1[N:13]1[CH2:14][CH2:15][O:16][CH2:17][CH2:18]1)#[N:10]

Participants

5

Reactant 3

HCID 12183Ethyl iodoacetateHCID 81531DiisopropylethylamineHCID 852399573-Morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrile

Product 1

HCID 68629708Ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylateYield 87%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 3-morpholin-4-yl-2-(morpholin-4-ylcarbonothioyl)acrylonitrile (0.07 g, 0.26 mmol), ethyl iodoacetate (0.034 mL, 0.29 mmol) and DIPEA (0.091 mL, 0.52 mmol) in ACN (0.55 mL) was subjected to MWI at 120° C. for 10 min. The crystals formed upon cooling were filtered, washed with cold MeOH and diethyl ether to give ethyl 4-cyano-5-morpholin-4-ylthiophene-2-carboxylate (0.06 g, 87%). LCMS: (AA) ES+ 267.1. 1H NMR (400 MHz, CDCl3) δ: 7.62 s, 1H), 4.30 (q, 2H), 3.85-3.87 (m, 4H), 3.58-3.60 (m, 4H) and 1.34 (t, 3H).

Workup

  1. customThe crystals formed
  2. temperatureupon cooling
  3. filtrationwere filtered
  4. washwashed with cold MeOH and diethyl ether

Sources & evidence

ORD record
ord-6aa1f85459df43908abba506c75312ec
Source dataset
uspto-grants-2015_05
Patent number
US09029411B2

Reaction notes

Loading…