Triethylamine → HCID 86689955, compound

HRID 716848Notes

Reaction equation

HRID 716848 reaction equation
Cl.[Cl:2][CH2:3][CH2:4][N:5]([CH2:13][CH2:14][Cl:15])[C:6]1[CH:11]=[CH:10][C:9]([NH2:12])=[CH:8][CH:7]=1.C(N(CC)CC)C.[N+:23]([C:26]1[CH:27]=[C:28]([N:32]=[C:33]=[O:34])[CH:29]=[CH:30][CH:31]=1)([O-:25])=[O:24]>C(Cl)(Cl)Cl>[Cl:2][CH2:3][CH2:4][N:5]([CH2:13][CH2:14][Cl:15])[C:6]1[CH:11]=[CH:10][C:9]([NH:12][C:33]([NH:32][C:28]2[CH:29]=[CH:30][CH:31]=[C:26]([N+:23]([O-:25])=[O:24])[CH:27]=2)=[O:34])=[CH:8][CH:7]=1

Participants

5

Reactant 3

HCID 8471Triethylamine2×HCID 768353-Nitrophenyl isocyanateHCID 2157271,4-Benzenediamine, N1,N1-bis(2-chloroethyl)-, hydrochloride (1:?)

Product 1

HCID 86689955HCID 86689955, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

To a stirred mixture of N-mustard amine 18 (7.66 g, 25 mmol) and triethylamine (TEA, (4 mL, 27.5 mmol) in CHCl3 (100 mL) was added a solution of 3-nitrophenyl isocyanate 44a (4.1 g, 25 mmol) in CHCl3 (50 mL) dropwise at room temperature. After being stirred additional 40-45 minutes, the solvent was removed by evaporation under reduced pressure and the solid residue was triturated with saturated aqueous solution of NaHCO3 and then collected by filtration. The solid was washed with water, hexane, and dried. The solid was recrystallized from ethyl acetate to give 1-(4-(bis(2-chloroethyl)amino)phenyl)-3-(3-nitrophenyl)urea (45a), 9.1 g (92%); mp 246-247° C. 1H NMR (DMSO-d6) δ: 3.69-3.71 (8H, m, CH2), 6.71-6.74 (2H, d, J=9.0 Hz, Ar—H), 7.29-7.31 (2H, d, J=8.9 Hz, Ar—H), 7.52-7.56 (1H, t, J=8.1 and 8.2 Hz, Ar—H), 7.69-7.71 (1H, d, J=8.0 Hz, Ar—H), 7.78-7.80 (1H, q, J=8.2 and 1.8 Hz, Ar—H), 8.52 (1H, brs, NH), 8.54-8.55 (1H, d, J=2 Hz, Ar—H), 9.11 (1H, brs, NH).

Workup

  1. customthe solvent was removed by evaporation under reduced pressure
  2. customthe solid residue was triturated with saturated aqueous solution of NaHCO3
  3. filtrationcollected by filtration
  4. washThe solid was washed with water, hexane
  5. customdried
  6. customThe solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-caa95338fbaf42c9aeaf34608e64564d
Source dataset
uspto-grants-2015_11
Patent number
US09193687B2

Reaction notes

Loading…