Isopropylamine → HCID 12791033, compound

HRID 1155235Notes

Reaction equation

HRID 1155235 reaction equation
[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][P:8](Cl)(Cl)=[O:9])[CH3:2].[CH:23]([NH2:26])([CH3:25])[CH3:24]>C(OCC)C>[CH2:1]([O:3][C:4](=[O:22])[CH2:5][N:6]([C:12]([S:14][CH2:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:13])[CH2:7][P:8]([NH:26][CH:23]([CH3:25])[CH3:24])([NH:26][CH:23]([CH3:25])[CH3:24])=[O:9])[CH3:2]

Participants

4

Reactant 2

HCID 6363IsopropylamineHCID 12791028HCID 12791028, compound

Product 1

HCID 12791033HCID 12791033, compoundYield 60.4%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent2×

Conditions

Temperature
25 °C

Procedure

Freshly prepared ethyl-N-[(benzylthio)carbonyl]-N-[dichlorophosphinylmethyl]-glycinate (10.5 g.; 0.027 mol.) dissolved in 100 ml. of diethyl ether was added to a solution containing isopropylamine (6.7 g.; 0.11 mol.) in 50 ml. of diethyl ether. The reaction mixture was stirred for 2 hours at 25° C., then filtered. The filtrate was washed with 5% sodium bicarbonate, then water. The ether layer was separated, dried over sodium sulfate and concentrated in vacuo. To remove remaining traces of solvent, the residue was concentrated at 25° C. and 0.05 mm. and yielded ethyl-N-[(benzylthio)carbonyl]-N-[bis(isopropylamino)phosphinylmethyl]-glycinate (7.0 g.) as crystals having a melting point of 69°-72° C. and the following analysis:

Workup

  1. filtrationfiltered
  2. washThe filtrate was washed with 5% sodium bicarbonate
  3. customThe ether layer was separated
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated in vacuo
  6. customTo remove
  7. concentrationthe residue was concentrated at 25° C.

Sources & evidence

ORD record
ord-1e58ab031c934e229e75b5b23387fead
Source dataset
uspto-grants-1981_11
Patent number
US04300942

Reaction notes

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