Benzyl chloroformate → HCID 22060503, compound

HRID 1782858Notes

Reaction equation

HRID 1782858 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([OH:9])[CH:5]=[C:6]([OH:8])[CH:7]=1.C(=O)([O-])O.[Na+].Cl[C:16]([O:18][CH2:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)=[O:17]>C1COCC1.O>[OH:9][C:4]1[CH:3]=[C:2]([NH:1][C:16](=[O:17])[O:18][CH2:19][C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)[CH:7]=[C:6]([OH:8])[CH:5]=1

Participants

5

Reactant 3

HCID 10387Benzyl chloroformateHCID 4107515-Aminobenzene-1,3-diolHCID 516892Sodium Bicarbonate

Product 1

HCID 22060503HCID 22060503, compound

Reagents, catalysts & solvents 1

HCID 21881883Oxolane--water (1/1)Solvent

Procedure

To a mixture of 5-aminobenzene-1,3-diol (0.60 g, 3.7 mmole) and sodium hydrogencarbonate (1.4 g, 16 mmole) in THF/water (15 mL, 1:1 v/v) was added dropwise benzyl chloroformate 1.6 mL, 11 mmole). After 3 h at rt, THF was removed under vacuum and the remaining aqueous layer was extracted with ethyl acetate. Purification by column chromatography over silica gel provided benzyl N-(3,5-dihydroxyphenyl)carbamate. 1H NMR (CD3OD): δ 7.42-7.25 (m, 5H), 6.46 (d, 2H, J=2.4 Hz), 5.97-5.94 (m, 1H), 5.14 (s, 2H).

Workup

  1. customTHF was removed under vacuum
  2. extractionthe remaining aqueous layer was extracted with ethyl acetate
  3. customPurification by column chromatography over silica gel

Sources & evidence

ORD record
ord-36019a3ae0a64b5a87b2f10ee16f2a16
Source dataset
uspto-grants-2009_03
Patent number
US07498435B2

Reaction notes

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