Thionyl Chloride → HCID 86622504, compound

HRID 1160241Notes

Reaction equation

HRID 1160241 reaction equation
[N+:1]([C:4]1[CH:24]=[CH:23][C:7]([CH2:8][O:9][N:10]=[CH:11][C:12]2[CH:17]=[CH:16][C:15](/[CH:18]=[CH:19]/[C:20](O)=[O:21])=[CH:14][CH:13]=2)=[CH:6][CH:5]=1)([O-:3])=[O:2].O=S(Cl)Cl.CCN(C(C)C)C(C)C.C1(C(C2C=CC=CC=2)(C2C=CC=CC=2)[S:45][NH2:46])C=CC=CC=1>C(Cl)Cl>[SH:45][NH:46][C:20](=[O:21])/[CH:19]=[CH:18]/[C:15]1[CH:16]=[CH:17][C:12]([CH:11]=[N:10][O:9][CH2:8][C:7]2[CH:23]=[CH:24][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=2)=[CH:13][CH:14]=1

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81531DiisopropylethylamineHCID 342377TriphenylmethanesulfenamideHCID 86622495HCID 86622495, compound

Product 1

HCID 86622504HCID 86622504, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Compound (2E)-3-{4-[(4-Nitro-benzyloxyimino)-methyl]-phenyl}-N-tritylsulfanyl-acrylamide was obtained (0.050 g, 0.08 mmol, 26% yield) by reaction of intermediate C (2E)-3-[4-({[(4-nitrobenzyl)oxy]imino}-methyl)phenyl]acrylic acid (ST3075, 0.100 g, 0.31 mmol) with SOCl2 (34 μL, 0.46 mmol), DIEA (236 μL, 1.38 mmol) and Triphenylmethanesulfenamide (0.098 g, 0.14 mmol) in anhydrous DCM at room temperature.

Sources & evidence

ORD record
ord-5f7f42f7c5244316add81e55f612693f
Source dataset
uspto-grants-2010_10
Patent number
US07816386B2

Reaction notes

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