Triethylamine → HCID 135530190, compound

HRID 2387000Notes

Reaction equation

HRID 2387000 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].[CH3:11]SC(=N)N.C(N([CH2:21][CH3:22])CC)C.[O:23]1[CH2:28][CH2:27]OCC1>>[CH3:6][S:7][C:8]1[NH:9][C:28](=[O:23])[C:27]2[CH2:22][CH2:21][C:11]=2[N:10]=1

Participants

4

Reactant 3

HCID 8471TriethylamineHCID 13347Bis(S-methylisothiouronium) sulfate2×HCID 312751,4-Dioxane

Product 1

HCID 135530190HCID 135530190, compoundYield 74%

Conditions

Temperature
50 °C

Procedure

In 50 mL of dry reaction flask methyl 2-chloro-2-cyclopropylidineacetate (365 mg, 2.50 mmol), S-methylisothiourea hemisulphate (see formula 2g) (1.392 g, 5.00 mmol) and triethylamine (1.52 g, 15.0 mmol) in 25 mL of anhydrous dioxane are stirred at 50° C. for 48 h. After filtration, the solid residue is suspended in DCM (25 mL) and washed with water. The aq. layer is extracted with DCM (2×25 mL). After removing the solvent in vacuum, the crude product is subjected to column chromatography (Rf=0.3, DCM/MeOH=25:1, 1.5×30 cm, 30 g SiO2) to yield 310 mg (74%) of the compound of formula 3g as a white solid, m.p. 215° C. —IR (KBr): nu(tilde)=2996 cm−1, 2928, 1654, 1541, 1456, 1396, 1297, 1189, 922, 751. —1H NMR (250 MHz, CDCl3): δ=2.58 (s, 3H, SMe), 2.95 (t, J=3.1 Hz, 2H, CH2), 3.15 (t, J=3.1 Hz, 2H, CH2), 11.5 (br. s, 1H, NH). —13C NMR (62.9 MHz, [D6]DMSO): 13.4 (+), 24.9 (−), 33.2 (+), 120.4 (C-6), 152.3 (C-1/C-3), 156.6 (C-3/C-1), 164.98 (C-5). —MS (70 eV), m/z (%): 169 (12) [M++1], 168 (100) [M+], 121 (14) [M+−SMe], 93 (22), 74 (16). —C7H8N2OS (168.2): calcd. C, 49.98; H, 4.79; N, 16.65. found C, 49.66; H, 5.14; N, 16.50.

Workup

  1. filtrationAfter filtration
  2. washwashed with water
  3. extractionThe aq. layer is extracted with DCM (2×25 mL)
  4. customAfter removing the solvent in vacuum

Sources & evidence

ORD record
ord-9d0f02696f2546768b28d170156efee2
Source dataset
uspto-grants-2012_09
Patent number
US08268845B2

Reaction notes

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