Methanol → HCID 53840544, compound

HRID 2257696Notes

Reaction equation

HRID 2257696 reaction equation
[CH2:1]([S:8][C:9]1[C:18]([NH:19][CH:20]=O)=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CO>C(Cl)(Cl)Cl>[CH2:1]([S:8][C:9]1[C:18]([NH:19][CH3:20])=[CH:17][CH:16]=[CH:15][C:10]=1[C:11]([O:13][CH3:14])=[O:12])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 887MethanolHCID 53962154HCID 53962154, compound

Product 1

HCID 53840544HCID 53840544, compoundYield 93.1%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
60 °C

Procedure

20 ml of borane/dimethyl sulfide complex (BMS) are added dropwise to a solution of 61.5 g of methyl 2-benzylmercapto-3-formylaminobenzoate (cf. Example d)) in 100 ml of CHCl3 at 0° C. The mixture is subsequently heated at 60° C. for 2 h, a further 20 ml of BMS are added, and the mixture is stirred at this temperature for a further 2.5 h. Then 30 ml of MeOH are added dropwise at 0° C. The mixture is transferred to a separating funnel, washed with water and brine and then dried over MgSO4. Volatile components are removed by distillation to give 54.60 g of methyl 2-benzylmercapto-3-methylaminobenzoate in the form of a yellowish oil. 1H NMR (CDCl3, 80 MHz): δ:2.6 (d, 3H, NH-CH3), 3.8 (s, 3H, OCH3), 3.9 (s, 2H, SCH2Ph), 5.2 (s, broad, 1H, NH-Me), 6.5 (d, 1H, Harom.), 6.8 (d, 1H, Harom.), 7.0-7.4 (m, 6H, Harom.).

Workup

  1. additiona further 20 ml of BMS are added
  2. customThe mixture is transferred to a separating funnel
  3. washwashed with water and brine
  4. dry with materialdried over MgSO4
  5. customVolatile components are removed by distillation

Sources & evidence

ORD record
ord-0da73605cc784beba10f7308496891f1
Source dataset
uspto-grants-1997_08
Patent number
US05658854

Reaction notes

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