Hydrochloric Acid → thioacetic acid S-cyclopropylcarbamoylmethyl ester

HRID 656632Notes

Reaction equation

HRID 656632 reaction equation
Cl[CH2:2][C:3]([NH:5][CH:6]1[CH2:8][CH2:7]1)=[O:4].[C:9]([OH:14])(=[S:13])[CH:10](C)O.O.Cl>ClCCl>[CH:6]1([NH:5][C:3]([CH2:2][S:13][C:9](=[O:14])[CH3:10])=[O:4])[CH2:8][CH2:7]1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 7357802-chloro-N-cyclopropylacetamideHCID 178473673HCID 178473673, compound

Product 1

HCID 57664398thioacetic acid S-cyclopropylcarbamoylmethyl esterYield 99%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 2-chloro-N-cyclopropyl-acetamide (58.1 g, 0.435 mol) in dichloromethane (700 ml) at 0° C. is added thiolactic acid (49.65 g, 0.652 mol). The mixture is stirred at 0° C. for 5 minutes, then TEA (88.0 g, 0.870 mol) is added very slowly (exothermic reaction). The mixture is stirred at 0° C. for 2 hours, then poured over 700 ml of water with stirring. The aqueous layer is acidified to pH2 with 5 N HCl, and the layers are shaken and separated. The aqueous layer is extracted with dichloromethane (2×400 ml). The combined organic layers are washed with brine, then dried (anhydrous magnesium sulfate), filtered, and concentrated to give the title compound as a yellow-orange solid (74.5 g, 99%). Mass (m/z): 174.1 (M++1).

Workup

  1. custom(exothermic reaction)
  2. stirringThe mixture is stirred at 0° C. for 2 hours
  3. stirringwith stirring
  4. stirringthe layers are shaken
  5. customseparated
  6. extractionThe aqueous layer is extracted with dichloromethane (2×400 ml)
  7. washThe combined organic layers are washed with brine
  8. dry with materialdried (anhydrous magnesium sulfate)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-394bf3e36f3a4b91814dd77bd6ddfbb9
Source dataset
uspto-grants-2011_12
Patent number
US08071776B2

Reaction notes

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