Triethylamine → HCID 2315017, compound

HRID 1287312Notes

Reaction equation

HRID 1287312 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][CH:12]=1)[C:7](Cl)=[O:8])([O-:3])=[O:2].[CH2:13]([O:15][P:16]([C:21]([NH2:24])([CH3:23])[CH3:22])(=[O:20])[O:17][CH2:18][CH3:19])[CH3:14].C(N(CC)CC)C>C(#N)C>[CH2:18]([O:17][P:16]([C:21]([NH:24][C:7](=[O:8])[C:6]1[CH:10]=[CH:11][CH:12]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)([CH3:22])[CH3:23])(=[O:20])[O:15][CH2:13][CH3:14])[CH3:19]

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 8495Benzoyl chloride, 3-nitro-HCID 25028516814-09-8

Product 1

HCID 2315017HCID 2315017, compoundYield 64.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Conditions

Temperature
0 °C

Procedure

83 g of 3-nitrobenzoyl chloride in 150 ml of acetonitrile are added dropwise to a solution of 105 g of 2-aminopropane-2-phosphonic acid diethyl ester and 45 g of triethylamine in 300 ml of acetonitrile at 0° C, with good stirring. After completion of the addition, the mixture is stirred for a further 3 hours at 0° C; it is then filtered and the solvent is distilled off in vacuo. The residue is purified by extraction by shaking with ether and aqueous 2 normal sodium carbonate solution. 99 g of 2-(3'-nitrobenzamido)propane-2-phosphonic acid diethyl ester of melting point 95°-96° C are obtained. This product is reduced with hydrogen as indicated in Example 2.

Workup

  1. additionAfter completion of the addition
  2. filtrationit is then filtered
  3. distillationthe solvent is distilled off in vacuo
  4. customThe residue is purified by extraction
  5. stirringby shaking with ether and aqueous 2 normal sodium carbonate solution

Sources & evidence

ORD record
ord-c015bd59a9fd46b0945f009495a73a9b
Source dataset
uspto-grants-1976_10
Patent number
US03984432

Reaction notes

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