Methylamine → Carbaryl

HRID 1680127Notes

Reaction equation

HRID 1680127 reaction equation
[C:1]1([OH:11])[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1.[C:12](Cl)(Cl)=[O:13].[CH3:16][NH2:17]>C1(C)C=CC=CC=1>[CH3:16][NH:17][C:12]([O:11][C:1]1[CH:2]=[CH:3][CH:4]=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:10]=12)=[O:13]

Participants

5

Reactant 3

HCID 6329MethylamineHCID 6371PhosgeneHCID 70051-Naphthol

Product 1

HCID 6129Carbaryl

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A stirred solution of 1-naphthol (86.5 g, 0.6 mole) in 500 g of toluene was heated under nitrogen to 98° C. Phosgene (79.9 g, 0.8 mole) and methylamine (22.0 g, 0.7 mole) were then metered into this solution concurrently and gradually over a period of approximately 6.5 hours. The reaction mixture was filtered hot. The filtrate was then allowed to cool to room temperature, and the crystallized carbaryl was recovered by filtration. The yield of 1-naphthyl methylcarbamate was 78%.

Workup

  1. filtrationThe reaction mixture was filtered hot
  2. filtrationthe crystallized carbaryl was recovered by filtration

Sources & evidence

ORD record
ord-c6471b32460d47168d8a32c77cb8ea99
Source dataset
uspto-grants-1981_06
Patent number
US04272441

Reaction notes

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