Triphenylphosphine → HCID 15382900, compound

HRID 1082047Notes

Reaction equation

HRID 1082047 reaction equation
O[CH2:2][CH:3]([NH:5]C(=O)OC(C)(C)C)[CH3:4].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.N(C(OCC)=O)=NC(OCC)=O.[Cl:44][C:45]1[C:50]([N+:51]([O-:53])=[O:52])=[CH:49][CH:48]=[CH:47][C:46]=1[OH:54]>C1C=CC=CC=1>[Cl:44][C:45]1[C:50]([N+:51]([O-:53])=[O:52])=[CH:49][CH:48]=[CH:47][C:46]=1[O:54][CH2:2][CH:3]([NH2:5])[CH3:4]

Participants

6

Reactant 4

HCID 11776TriphenylphosphineHCID 220568ethyl N-ethoxycarbonyliminocarbamateHCID 545701tert-butyl N-(1-hydroxypropan-2-yl)carbamateHCID 3013917Phenol, 2-chloro-3-nitro-

Product 1

HCID 15382900HCID 15382900, compoundYield 96.3%

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Conditions

Temperature
80 °C

Procedure

7.2 g (0.0414 mol) of 1,1-dimethylethyl 2-hydroxy-1-methylethylcarbamate and 10.8 g (0.0414 mol) 15 of triphenylphosphine are placed in a 500 ml, three-necked, round-bottomed flask containing 140 ml of benzene. The mixture is cooled in an ice bath and 6.5 ml (0.0414 mol) of diethyl azodicarboxylate are added dropwise. The mixture is left stirring for 15 minutes, 4.8 g (0.027 mol) of 2-chloro-3-nitrophenol are added, the temperature of the reaction mixture is left to return to room temperature and the reaction mixture is left stirring overnight. The precipitate obtained is then filtered and the filtrate evaporated. The residue is taken up in 100 ml of a 3N hydrochloric acid solution and is then heated at 80° C. in an oil bath for 2 hours. The phases are separated, the aqueous phase is recovered, the pH is adjusted to alkaline with a concentrated sodium hydroxide solution and extraction is carried out three times with ether. Washing is carried out with water and drying is carried out. There are obtained 6 g of product which is used as is in the following stage.

Workup

  1. temperatureThe mixture is cooled in an ice bath
  2. waitThe mixture is left
  3. waitthe temperature of the reaction mixture is left
  4. customto return to room temperature
  5. waitthe reaction mixture is left
  6. stirringstirring overnight
  7. customThe precipitate obtained
  8. filtrationis then filtered
  9. customthe filtrate evaporated
  10. customThe phases are separated
  11. customthe aqueous phase is recovered
  12. extractionto alkaline with a concentrated sodium hydroxide solution and extraction
  13. washWashing
  14. customdrying

Sources & evidence

ORD record
ord-48799092521c4e66b596d5770eff8214
Source dataset
uspto-grants-1996_12
Patent number
US05589476

Reaction notes

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