Hydrochloric Acid → 2-chloro-N-(5-methoxy-2-methylphenyl)acetamide

HRID 1267921Notes

Reaction equation

HRID 1267921 reaction equation
[CH3:1][C:2]1[CH:8]=[CH:7][C:6]([O:9][CH3:10])=[CH:5][C:3]=1[NH2:4].C(N(C(C)C)CC)(C)C.[Cl:20][CH2:21][C:22](Cl)=[O:23].Cl>O1CCCC1>[Cl:20][CH2:21][C:22]([NH:4][C:3]1[CH:5]=[C:6]([O:9][CH3:10])[CH:7]=[CH:8][C:2]=1[CH3:1])=[O:23]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 6577Chloroacetyl chlorideHCID 81531DiisopropylethylamineHCID 995005-Methoxy-o-toluidine

Product 1

HCID 11328892-chloro-N-(5-methoxy-2-methylphenyl)acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2-methyl-5-methoxyaniline (4.7 g) in tetrahydrofuran (50 ml), under nitrogen, was added diisopropylethylamine (12.6 ml) followed by dropwise addition of chloroacetyl chloride (2.7 ml) and the mixture stirred under nitrogen for 27 hours. The solution was poured into 2M aqueous hydrochloric acid (150 ml), extracted into diethyl ether (3×150 ml), washed with brine, dried (MgSO4), and concentrated to give the sub-title compound as a brown oil (5.15 g).

Workup

  1. extractionextracted into diethyl ether (3×150 ml)
  2. washwashed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-36a1ed5f78f94422bbb65456f266ec6b
Source dataset
uspto-grants-2003_04
Patent number
US06555541B1

Reaction notes

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