Water → Ethyl 2-(dichloromethyl)-4,5-dihydro-1,3-thiazole-4-carboxylate

HRID 902771Notes

Reaction equation

HRID 902771 reaction equation
[Cl:1][CH:2]([Cl:5])[C:3]#[N:4].C[O-].[Na+].Cl.[CH2:10]([O:12][C:13](=[O:18])[C@H:14]([CH2:16][SH:17])N)[CH3:11].O>CO.C(Cl)Cl>[Cl:1][CH:2]([Cl:5])[C:3]1[S:17][CH2:16][CH:14]([C:13]([O:12][CH2:10][CH3:11])=[O:18])[N:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 18177DichloroacetonitrileHCID 2723617Ethyl cysteinate hydrochlorideHCID 10942334Sodium Methoxide

Product 1

HCID 67420856Ethyl 2-(dichloromethyl)-4,5-dihydro-1,3-thiazole-4-carboxylateYield 93%

Reagents, catalysts & solvents 2

HCID 887MethanolSolvent2×HCID 6344DichloromethaneSolvent

Procedure

Dichloroacetonitrile (33.67 mL, 420 mmol) was added slowly, whilst maintaining the temperature below 0° C., over 30 min. to a solution of sodium methoxide ((25% w/w) 9.63 mL, 43 mmol) in methanol (84.5 mL) which was precooled to −10° C. This was allowd to stir for 30 min. before the addition of L-cysteine ethyl ester hydrochloride (78.32 g, 422 mmol) dissolved in methanol (67.4 mL) and then stirred overnight at RT. Water (136 mL) followed by DCM (136 mL) was added to the mixture and stirred vigorously. The organic layer was separated and the aqueous layer was reextracted with a further 136 mL of DCM. This was concentrated in vacuo to give the crude product (94.1 g, 93%).

Workup

  1. temperaturewhilst maintaining the temperature below 0° C.
  2. additionwas added to the mixture
  3. stirringstirred vigorously
  4. customThe organic layer was separated
  5. concentrationThis was concentrated in vacuo

Sources & evidence

ORD record
ord-decbb317192d4b52a198f9191afcd123
Source dataset
uspto-grants-2008_04
Patent number
US07365225B2

Reaction notes

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