2-Methylphenyl isothiocyanate → Ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoate

HRID 987529Notes

Reaction equation

HRID 987529 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][C:3]=1[OH:15].[C:16]1([CH3:25])[C:17]([N:22]=[C:23]=S)=[CH:18][CH:19]=[CH:20][CH:21]=1>C(O)C>[C:16]1([CH3:25])[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[NH:22][C:23]1[O:15][C:3]2[CH:4]=[C:5]([CH2:8][CH2:9][C:10]([O:12][CH2:13][CH3:14])=[O:11])[CH:6]=[CH:7][C:2]=2[N:1]=1

Participants

4

Reactant 2

HCID 691952-Methylphenyl isothiocyanateHCID 18008946Ethyl 4-amino-3-hydroxybenzenepropionate

Product 1

HCID 18008945Ethyl 3-(2-o-tolylamino-benzoxazol-6-yl)propanoateYield 53.2%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
40 °C

Procedure

A solution of ethyl 3-(4-amino-3-hydroxyphenyl)-propionate (1.94 g) in ethanol (50 ml) was treated with o-tolyl isothiocyanate (1.66 g) and then heated at 40° C. for 2 hours. The mixture was evaporated then treated with ethanol (50 ml), then with diisopropylcarbodiimide (3 mL) and then stirred at 40° C. for 1 hour. The mixture was evaporated and the residue was treated with diethyl ether (50 ml) then filtered. The filtrate was evaporated to dryness and the residue subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:3, v/v) to give the title compound (1.6 g) as a colourless oil.

Workup

  1. customThe mixture was evaporated
  2. additionthen treated with ethanol (50 ml)
  3. customThe mixture was evaporated
  4. additionthe residue was treated with diethyl ether (50 ml)
  5. filtrationthen filtered
  6. customThe filtrate was evaporated to dryness
  7. additionthe residue subjected to flash chromatography on silica eluting with a mixture of ethyl acetate and cyclohexane (2:3

Sources & evidence

ORD record
ord-72c13aa1016e45db92d5c638f1fc8c46
Source dataset
uspto-grants-2003_10
Patent number
US06632814B1

Reaction notes

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