Thionyl Chloride → HCID 59418741, compound

HRID 2209120Notes

Reaction equation

HRID 2209120 reaction equation
[NH2:1][C:2]1[CH:7]=[C:6]([Br:8])[CH:5]=[CH:4][C:3]=1[N:9]([CH3:13])[CH2:10][CH2:11]O.S(Cl)([Cl:16])=O>C(Cl)Cl.CN(C=O)C>[Br:8][C:6]1[CH:7]=[C:2]([NH2:1])[C:3]([N:9]([CH2:10][CH2:11][Cl:16])[CH3:13])=[CH:4][CH:5]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 43345909HCID 43345909, compound

Product 1

HCID 59418741HCID 59418741, compoundYield 96.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 6344DichloromethaneSolvent

Procedure

2-((2-amino-4-bromophenyl)(methyl)amino)ethanol (3.09 g, 0.013 mol) was dissolved in DCM (100 mL) with DMF (10 drop), Thionyl chloride (1.8 g, 0.015 mol in 10 ml DCM) was added dropwise at 0° C. The reaction was stirred at rt for 10 min then 80° C. for 30 min, rt for 16 h. The mixture was partitioned between 1N NaOH and DCM (2×30 ml). The combined organic layers was concentrated to give 3.2 g, (96.3%) of 4-bromo-N1-(2-chloroethyl)-N1-methylbenzene-1,2-diamine LCMS-ESI+ (m/z): [M+H]+ calcd for C9H12BrClN2:261.99; found 262.9.

Workup

  1. additionwas added dropwise at 0° C
  2. wait80° C. for 30 min
  3. waitrt for 16 h
  4. customThe mixture was partitioned between 1N NaOH and DCM (2×30 ml)
  5. concentrationThe combined organic layers was concentrated

Sources & evidence

ORD record
ord-c78ff5fc94e34eb0b4948cea4d1cdf5a
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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