Cyclohexane → HCID 54227761, compound

HRID 1658022Notes

Reaction equation

HRID 1658022 reaction equation
C(=[N:8][CH:9]([P:23]([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)([O:25][C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)=[O:24])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11])C1C=CC=CC=1.O.C1(C)C=CC(S(O)(=O)=O)=CC=1.C1CCCCC1>C(OCC)C>[NH2:8][CH:9]([P:23]([O:25][C:26]1[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=1)([O:32][C:33]1[CH:38]=[CH:37][CH:36]=[CH:35][CH:34]=1)=[O:24])[C:10]([O:12][CH2:13][C:14]1[CH:19]=[CH:18][C:17]([N+:20]([O-:22])=[O:21])=[CH:16][CH:15]=1)=[O:11]

Participants

5

Reactant 3

HCID 8078CyclohexaneHCID 521998p-Toluenesulfonic acid monohydrateHCID 54211819HCID 54211819, compound

Product 1

HCID 54227761HCID 54227761, compound

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Procedure

A solution of p-nitrobenzyl N-benzylidene-α-aminodiphenylphosphonoacetate (16.43 g) in ethyl ether (100 ml) is added dropwise over 30 minutes to a stirring solution of p-toluenesulfonic acid monohydrate (6.48 g) in ethyl ether (150 ml). Cyclohexane (100 ml) is added to the mixture and the solvents are decanted from the precipitate. The precipitate is washed with more 2:1 ethyl ether-cyclohexane which is again decanted off. The precipitate is treated with 1 M aqueous dipotassium hydrogen phosphate (60 ml) and extracted with four portions of methylene chloride. The methylene chloride solution is dried over magnesium sulfate, filtered, and evaporated to give p-nitrobenzyl α-aminodiphenylphosphonacetate.

Workup

  1. customthe solvents are decanted from the precipitate
  2. washThe precipitate is washed with more 2:1 ethyl ether-cyclohexane which
  3. customis again decanted off
  4. additionThe precipitate is treated with 1 M aqueous dipotassium hydrogen phosphate (60 ml)
  5. extractionextracted with four portions of methylene chloride
  6. dry with materialThe methylene chloride solution is dried over magnesium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customto give p-nitrobenzyl α-aminodiphenylphosphonacetate

Sources & evidence

ORD record
ord-6722a63cf2ac4628b79726730a1a5ee2
Source dataset
uspto-grants-1976_06
Patent number
US03962224

Reaction notes

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