3-Chloropropionyl chloride → 5-Bromo-2-(2-Chloroethyl)-1-methyl-1H-naphth[1,2-d]imidazole

HRID 2198998Notes

Reaction equation

HRID 2198998 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]([NH:12][CH3:13])=[C:4]([N+:14]([O-])=O)[CH:3]=1.[Cl:17][CH2:18][CH2:19][C:20](Cl)=O>>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2[N:12]([CH3:13])[C:20]([CH2:19][CH2:18][Cl:17])=[N:14][C:4]=2[CH:3]=1

Participants

3

Reactant 2

HCID 693643-Chloropropionyl chlorideHCID 138061824-bromo-N-methyl-2-nitro-1-naphthylamine

Product 1

HCID 140724875-Bromo-2-(2-Chloroethyl)-1-methyl-1H-naphth[1,2-d]imidazole

Conditions

Temperature
80 °C

Procedure

A mixture of 80.3 g (0.286 mole) of 4-bromo-N-methyl-2-nitro-1-naphthylamine, prepared as described in the first part of Example 36, and 41 cc (0.426 mole) of 3-chloropropanoyl chloride is stirred for 2 hours at 60° C. and for a further 2 hours at 80° C. The excess of acyl chloride is distilled off at 40° C. under vacuum and the residue, taken up with methylene chloride, is washed first with a saturated NaHCO3 solution and then with water.

Workup

  1. customprepared
  2. distillationThe excess of acyl chloride is distilled off at 40° C. under vacuum
  3. washis washed first with a saturated NaHCO3 solution

Sources & evidence

ORD record
ord-794c6b33b3704c1e8ae4195ca931e16d
Source dataset
uspto-grants-1982_11
Patent number
US04360674

Reaction notes

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