Chloroacetonitrile → 4-[2-(Benzyloxycarbonylamino)-ethyl]-phenoxyacetonitrile

HRID 2248127Notes

Reaction equation

HRID 2248127 reaction equation
[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([OH:20])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.CC[O-].[Na+].[Na].Cl[CH2:27][C:28]#[N:29]>C(OCC)C.C(O)C>[CH2:1]([O:8][C:9]([NH:11][CH2:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH2:27][C:28]#[N:29])=[CH:16][CH:15]=1)=[O:10])[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7856ChloroacetonitrileHCID 2723922Sodium ethoxideHCID 5360545SodiumHCID 14103856Benzyl [2-(4-hydroxyphenyl)ethyl]carbamate

Product 1

HCID 145562024-[2-(Benzyloxycarbonylamino)-ethyl]-phenoxyacetonitrile

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 3283Diethyl EtherSolvent

Procedure

48.82 g. (0.18 mol) of the above-prepared N-(benzyloxycarbonyl)-p-hydroxyphenethylamine are introduced into a sodium ethylate solution freshly prepared from 5.17 g. sodium and 270 ml. ethanol, 11.4 ml. (0.18 mol) chloroacetonitrile are slowly added dropwise thereto and the reaction mixture is heated to the boil. After 5 hours, the solvent is stripped off, the residue is taken up in diethyl ether, extracted twice with 2N aqueous sodium hydroxide solution, washed neutral, dried over anhydrous sodium sulphate and evaporated to dryness. The oily residue is recrystallised from ligroin/diethyl ether (8:2 v/v). There are obtained 44.74 g. (80% of theory) of the desired product in the form of colourless crystals; m.p. 110°-115° C.

Workup

  1. customfreshly prepared from 5.17 g
  2. temperaturethe reaction mixture is heated to the boil
  3. extractionextracted twice with 2N aqueous sodium hydroxide solution
  4. washwashed neutral
  5. dry with materialdried over anhydrous sodium sulphate
  6. customevaporated to dryness
  7. customThe oily residue is recrystallised from ligroin/diethyl ether (8:2 v/v)
  8. customThere are obtained 44.74 g

Sources & evidence

ORD record
ord-1b510b0af09943ddaece359eb630088d
Source dataset
uspto-grants-1991_08
Patent number
US05037990

Reaction notes

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