Water → HCID 152766194, compound

HRID 2367114Notes

Reaction equation

HRID 2367114 reaction equation
S(O)(O)(=O)=O.[CH3:6][S:7][C:8](=[NH:10])[NH2:9].O.Cl[C:13]([O:15][CH2:16][CH2:17][CH2:18][Cl:19])=[O:14]>O1CCOCC1.C(OCC)(=O)C>[Cl:19][CH2:18][CH2:17][CH2:16][O:15][C:13](=[O:14])[NH:10][C:8](=[NH:9])[S:7][CH3:6]

Participants

6

Reactant 3

HCID 962WaterHCID 69399Carbonochloridic acid, 3-chloropropyl esterHCID 752702-Methyl-2-thiopseudourea sulfate

Product 1

HCID 152766194HCID 152766194, compoundYield 64.1%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-methyl-2-thiopseudourea sulfate (5.56 g, 20.0 mmol) in water (50 mL) sodium bicarbonate (6.73 g, 80.0 mmol) was added and the reaction mixture was cooled to 0° C. A solution of 3-chloropropyl chloroformate (2.41 mL, 20.0 mmol) in 1,4-dioxane (20 mL) was added dropwise and it was stirred for 15 hour at room temperature. The reaction mixture was diluted with ethyl acetate (250 mL) and the organic layer was separated. It was washed with water and brine, dried over anhydrous sodium sulfate and the solvent was evaporated. The resulting crude product was purified by silica gel flash chromatography (hexane:ethyl acetate 7:3 to 1:1 eluent) to give 3-chloropropyl[imino(methylthio)methyl]carbamate (2.70 g, 64% yield) as a white solid. 1H NMR (400 MHz, DMSO-d6): 8.58 (br.s, 1H), 4.06 (t, 2H), 3.67 (t, 1H), 2.32 (s, 3H), 2.02 m, 2H); MS (EI) for C6H11ClN2O2S: 211 (MH+).

Workup

  1. customthe organic layer was separated
  2. washIt was washed with water and brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customthe solvent was evaporated
  5. customThe resulting crude product was purified by silica gel flash chromatography (hexane:ethyl acetate 7:3 to 1:1 eluent)

Sources & evidence

ORD record
ord-c5318c3dc1ee4dfdbdc9f311f4f8269e
Source dataset
uspto-grants-2014_04
Patent number
US08697737B2

Reaction notes

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