Diethyl cyanophosphonate → HCID 22729209, compound

HRID 2085132Notes

Reaction equation

COC[O:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([OH:16])=O)[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1.Cl.[CH3:18][NH:19][O:20][CH3:21].P(C#N)(OCC)(OCC)=O>>[OH:4][C:5]1[C:13]2[CH:12]=[C:11]([C:14]([N:19]([O:20][CH3:21])[CH3:18])=[O:16])[S:10][C:9]=2[CH:8]=[CH:7][CH:6]=1

Participants

Reactant 3

HCID 76257Diethyl cyanophosphonate

HCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)

HCID 22728980HCID 22728980, compound

Product 1

HCID 22729209HCID 22729209, compoundYield 89.3%

Procedure

By the reactions in the same manner as in Starting Material Synthesis Example 16 using 4-(methoxymethyloxy)-benzo(b)thiophene-2-carboxylic acid (4.5 g), N,O-dimethylhydroxylamine hydrochloride (2.1 g) and diethyl cyanophosphate (3.2 g), 4-hydroxy-N-methoxy-N-methylbenzo(b)-thiophene-2-carboxamide (4.0 g) was obtained as a brown oil. By the reactions in the same manner as in Starting Material Synthesis Example 1 using the brown oil (2.0 g) and (S)-glycidyl nosylate (2.0 g), the title compound (1.1 g) was obtained as brown crystals.

Sources & evidence

ORD record: ord-28f8e3a9cded4709860522c3e5886692
Source dataset: uspto-grants-2004_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06720320B2

Reaction notes

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