Iodine → Benzyl [2-(5-ethyloxazol-2-yl)ethyl]carbamate

HRID 1804554Notes

Reaction equation

HRID 1804554 reaction equation
C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.II.C(N(CC)CC)C.O=[C:30]([CH2:48][CH3:49])[CH2:31][NH:32][C:33]([CH2:35][CH2:36][NH:37][C:38](=[O:47])[O:39][CH2:40][C:41]1[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=1)=[O:34]>ClCCl>[CH2:48]([C:30]1[O:34][C:33]([CH2:35][CH2:36][NH:37][C:38](=[O:47])[O:39][CH2:40][C:41]2[CH:46]=[CH:45][CH:44]=[CH:43][CH:42]=2)=[N:32][CH:31]=1)[CH3:49]

Participants

6

Reactant 4

HCID 807IodineHCID 8471TriethylamineHCID 11776TriphenylphosphineHCID 57637089Benzyl [2-(2-oxobutylcarbamoyl)ethyl]carbamate

Product 1

HCID 57636953Benzyl [2-(5-ethyloxazol-2-yl)ethyl]carbamate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

23.07 g (49.60 mmol) PS-triphenylphosphine are suspended in 200 ml dichloromethane, 12.65 g (49.82 mmol) iodine are added. The mixture is stirred for 0.1 hours at ambient temperature, then 13.80 ml (99.28 mmol) triethylamine are added dropwise. 5.80 g (19.84 mmol) benzyl [2-(2-oxo-butylcarbamoyl)-ethyl]-carbamate dissolved in 150 ml dichloromethane are added. The reaction mixture is stirred for 72 hours at ambient temperature, then the precipitate is filtered off. The filtrate is extracted with water, the organic phase is dried and evaporated to dryness.

Workup

  1. additionare added
  2. stirringThe reaction mixture is stirred for 72 hours at ambient temperature
  3. filtrationthe precipitate is filtered off
  4. extractionThe filtrate is extracted with water
  5. customthe organic phase is dried
  6. customevaporated to dryness

Sources & evidence

ORD record
ord-344c509a61b94b95b2a986106514681b
Source dataset
uspto-grants-2013_01
Patent number
US08354418B2

Reaction notes

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