Trimethyl phosphite → Dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-semicarbazonopropylphosphonate

HRID 1375231Notes

Reaction equation

Cl[CH2:2][C:3](=[N:16][NH:17][C:18]([NH2:20])=[O:19])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([C:12]([F:15])([F:14])[F:13])[CH:7]=1.[P:21]([O:26]C)([O:24][CH3:25])[O:22][CH3:23]>C1(C)C=CC=CC=1>[F:13][C:12]([F:15])([F:14])[C:8]1[CH:7]=[C:6]([CH:11]=[CH:10][CH:9]=1)[O:5][CH2:4][C:3](=[N:16][NH:17][C:18]([NH2:20])=[O:19])[CH2:2][P:21](=[O:26])([O:24][CH3:25])[O:22][CH3:23]

Participants

Conditions

Temperature: 0 °C

Procedure

A mixture of 1-chloro-3-[3-(trifluoromethyl)phenoxy]-2-propanone semicarbazone (36.5 g, 0.12 mol), P(OMe)3 (18.6 g, 0.15 mol) and toluene (100 mL) was refluxed for 3 h and cooled to 0° C. The precipitate was filtered off, washed on the filter with cold toluene and recrystallized from toluene to afford 26.8 g (59%) of dimethyl 3-[3-(trifluoromethyl)phenoxy]-2-semicarbazonopropylphosphonate as about 10:1 mixture of two isomers: mp 132–133° C. 1H NMR (CDCl3) (major isomer) δ: 9.40 (s, 1H), 7.37 (t, J=8.0 Hz, 1H), 7.19 (d, J=8.0 Hz, 1H), 7.15 (s, 1H), 7.07 (d, J=8.0 Hz, 1H), 5.80 (br.s, 2H), 4.68 (s, 2H), 3.76 (s, 3H), 3.73 (s, 3H), 3.11 (d, J=12 Hz, 2H).

Workup

temperaturewas refluxed for 3 h
filtrationThe precipitate was filtered off
washwashed on the
filtrationfilter with cold toluene
customrecrystallized from toluene

Sources & evidence

ORD record: ord-74c69b55a5a1483380581beebb97dd24
Source dataset: uspto-grants-2007_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07166730B2

Reaction notes

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