Methyl chloroformate → HCID 53855308, compound

HRID 2257697Notes

Reaction equation

HRID 2257697 reaction equation
Cl[C:2]([O:4][CH3:5])=[O:3].[CH2:6]([S:13][C:14]1[C:23]([NH:24][CH3:25])=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.C(=O)([O-])O.[Na+]>>[CH2:6]([S:13][C:14]1[C:23]([NH:24][CH2:25][C:2]([O:4][CH3:5])=[O:3])=[CH:22][CH:21]=[CH:20][C:15]=1[C:16]([O:18][CH3:19])=[O:17])[C:7]1[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1

Participants

4

Reactant 3

HCID 6586Methyl chloroformateHCID 516892Sodium BicarbonateHCID 53840544HCID 53840544, compound

Product 1

HCID 53855308HCID 53855308, compound

Procedure

4.6 ml of methyl chloroformate are added dropwise to a suspension of 15.0 g (0.052 mol) of methyl 2-benzylmercapto-3-methylaminobenzoate and 5.88 g (0.07 mol) of sodium hydrogen carbonate in 100 ml of CH2CN. After 5 h volatile components are removed by distillation (15 torr, 40° C.). The residue is taken up in ethyl acetate and washed in succession with 1 N hydrochloric acid and water. The organic phase is dried over MgSO4 and then the solvent is removed by distillation. Methyl 2-benzylmercapto-3-(N-methoxycarbonylmethylamino)benzoate is obtained in the form of a yellowish oil )14.8 g); 1H NMR (CDCl3, 80 MHz): δ=3.0 (s, 3H, N-CH3), 3.6 (s, 3H, O-CH3), 3.9 (s, 5H, OCH3 and SCH2Ph), 7.1-7.6 (m, 8H, Harom.).

Workup

  1. customAfter 5 h volatile components are removed by distillation (15 torr, 40° C.)
  2. washwashed in succession with 1 N hydrochloric acid and water
  3. dry with materialThe organic phase is dried over MgSO4
  4. customthe solvent is removed by distillation

Sources & evidence

ORD record
ord-9ce606088e2e480db3abfc01dedb1272
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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