Hydrochloric Acid → HCID 86747082, compound

HRID 2253918Notes

Reaction equation

HRID 2253918 reaction equation
[CH3:1][NH:2][CH2:3][CH2:4][Cl:5].Cl.CN(CCCl)P(Cl)(Cl)=O.[CH3:16][C:17]1([CH3:32])[O:21][CH:20]([CH2:22][CH2:23][P:24]([Cl:31])(N(C)CCBr)=[O:25])[CH2:19][O:18]1>>[CH3:16][C:17]1([CH3:32])[O:21][CH:20]([CH2:22][CH2:23][P:24]([Cl:31])([N:2]([CH3:1])[CH2:3][CH2:4][Cl:5])=[O:25])[CH2:19][O:18]1

Participants

5

Reactant 4

HCID 313Hydrochloric AcidHCID 20652Ethanamine, 2-chloro-N-methyl-HCID 9990714HCID 9990714, compoundHCID 86747081[2-(2,2-dimethyl-1,3-dioxolan-4-yl)ethyl]-N-methyl-N-(2-bromoethyl)phosphoramidoyl chloride

Product 1

HCID 86747082HCID 86747082, compoundYield 61%

Procedure

This compound was prepared from N-methyl-N-chloroethylamine.HCl via N-methyl-N-(2-chloroethyl)phosphoramidic dichloride, as described for 16a (14 mmol scale). The crude residue was purified by chromatography (1:4 EtOAc:hexanes) to give 16b as an oil (2.72 g, 61%): Rf 0.75 (1:1 EtOAc:hexanes); 1H NMR (CDCl3) 4.22(m, 4H), 3.60(m, 3H), 3.42(m, 2H), 2.80(d, 3H, J=12.85 Hz), 1.99(dt, 2H, J=6.11 Hz), 1.36(d, 6H, J=15.82 Hz)ppm; -P NMR (CDCl3) -7.69, -7.92 ppm (1:1 ratio of diastereomers).

Workup

  1. customThe crude residue was purified by chromatography (1:4 EtOAc:hexanes)

Sources & evidence

ORD record
ord-9ae7fd4e9b2f4e48bcba8125ed132991
Source dataset
uspto-grants-1993_08
Patent number
US05233031

Reaction notes

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