Ammonia → HCID 373379, compound

HRID 1899063Notes

Reaction equation

HRID 1899063 reaction equation
[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][C:9]=1[N+:20]([O-:22])=[O:21])[CH2:5][CH2:6][Cl:7].[NH3:23]>CCOCC>[Cl:1][CH2:2][CH2:3][N:4]([C:8]1[C:16]([N+:17]([O-:19])=[O:18])=[CH:15][C:11]([C:12]([NH2:23])=[O:13])=[CH:10][C:9]=1[N+:20]([O-:22])=[O:21])[CH2:5][CH2:6][Cl:7]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 10736699HCID 10736699, compound2×

Product 1

HCID 373379HCID 373379, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 3283Diethyl EtherSolvent

Conditions

Temperature
5 °C

Procedure

The above acid (XV: X=Cl, Z=OH) was converted to the crude acid chloride (XV: X=Cl, Z=Cl), which was dissolved in dry Et2O (100 mL), cooled to 5° C., and treated dropwise with aqueous NH3 (20 mL of a 3N solution, 60 mmol). After 10 min the solution was worked up, and the residue was chromatographed on silica. Elution with EtOAc/petroleum ether (3:7) gave foreruns, while EtOAc/petroleum ether (7:3) gave 4-[N,N-bis(2-chloroethyl)amino]-3,5-dinitrobenzamide (23) (Ig: X=Cl, R=CONH2) (80% overall yield), mp (EtOAc/petroleum ether) 113°-116° C. 1H NMR (CD3COCD3) δ 8.61 (s, 2 H, H-2,6), 7.98, 7.24 (2xbr, 2 H, CONH2), 3.75 (t, J=7.0 Hz, 4 H, CH2Cl), 3.50 (t, 4 H, CH2N). 13C NMR δ 164.91 (CONH2), 149.32 (C-4), 140.07 (C-3,5), 132.18 (C-1), 128.91 (C-2,6), 56.37 (CH2N), 42.55 (CH2Cl). Anal. (C11H12Cl2N4O5) C,H,N,Cl.

Workup

  1. customthe residue was chromatographed on silica
  2. washElution with EtOAc/petroleum ether (3:7)
  3. customgave foreruns

Sources & evidence

ORD record
ord-81f7c5b82a5945f4874eaa43bbcc6054
Source dataset
uspto-grants-1996_11
Patent number
US05571845

Reaction notes

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