Thionyl Chloride → HCID 10339159, compound

HRID 1290332Notes

Reaction equation

HRID 1290332 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:20]([O-:22])=[O:21])=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13](O)=[O:14])[CH2:5][CH2:6][Cl:7].O=S(Cl)[Cl:25]>CN(C=O)C>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:9]([N+:20]([O-:22])=[O:21])=[CH:10][C:11]([N+:17]([O-:19])=[O:18])=[C:12]([CH:16]=1)[C:13]([Cl:25])=[O:14])[CH2:5][CH2:6][Cl:7]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 372567HCID 372567, compound

Product 1

HCID 10339159HCID 10339159, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Treatment of (6) with excess SOCl2 containing a drop of DMF under reflux for 20 min, followed by concentration to dryness and azeotroping with benzene, gave crude 5-[N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzoyl chloride (VI: X=Cl; Y1 =Cl). This was dissolved in Me2CO (20 ML), cooled to 0° C., treated with excess 40% aqueous methylamine. The product was purified by chromatography on silica gel, elution with EtOAc/petroleum ether (1:1) giving N-methyl [N,N-bis(2-chloroethyl)amino]-2,4-dinitrobenzamide (8) (Ib: X=Cl, R=CONHMe), mp (EtOAc/petroleum ether) 180.5° C. 1H NMR (CD3COCD3) δ8.53 (s, 1 H., ArH3), 7.75 (br, 1 H, CONH), 7.56 (s, 1H, H-6), 3.88-3.80 (m, 8 H, N-CHCH2CH2Cl), 2.90, 2.89 (2s, 3H, CONHMe). 13NMR δ165.89 (CONH), 148.43 (C-5), 140.05, 138.26 (C-2,4), 138.94 (C-1), 125.05, 122.45 (C-3,6), 54.20 (CH2N), 42.10 (CH2Cl), 26.69 (CONHCH3). Anal. (C12 H14Cl2N4O5) C,H,N,Cl.

Workup

  1. concentrationfollowed by concentration to dryness
  2. customazeotroping with benzene

Sources & evidence

ORD record
ord-f2292bdcb7ea43eb9577257387f11b46
Source dataset
uspto-grants-1998_05
Patent number
US05750782

Reaction notes

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