1-Naphthol → Carbaryl

HRID 1290269Notes

Reaction equation

HRID 1290269 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.[CH3:12][NH:13][C:14](=S)[OH:15].[Na]>C1C=CC=CC=1>[CH3:12][NH:13][C:14](=[O:15])[O:11][C:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 70051-NaphtholHCID 5360545SodiumHCID 178486072HCID 178486072, compound

Product 1

HCID 6129Carbaryl

Reagents, catalysts & solvents 1

HCID 241BenzeneSolvent

Procedure

To a solution of 1-naphthol (1.44 g, 0.01 mole) and S-methyl ester of N-methylcarbamothioic acid (1.575 g, 0.015 mole) in benzene (6 ml) there was added sodium (0.15 g) and the mixture was refluxed for 20 hrs. The reaction mixture was cooled and washed with water and a cold 5% NaOH solution followed by water and brine and then dried. The removal of solvent afforded the solid which was further purified by crystallization to furnish 1-naphthyl N-methylcarbamate of the formula VII, m.p. 140-141° C., IR: 3305 (N-H), 1715 (-COO-), 1600, 1540, 770 (aromatic): PMR (CdCl3, 90 MHz), 2.86 (3H, d, J=1Hz, NH-CH3, 5.14 (1H, br s, N-H) and 7.17 to 8 (7H, m, aromatic).

Workup

  1. temperaturethe mixture was refluxed for 20 hrs
  2. temperatureThe reaction mixture was cooled
  3. washwashed with water
  4. customdried
  5. customThe removal of solvent
  6. customafforded the solid which
  7. customwas further purified by crystallization

Sources & evidence

ORD record
ord-f1e9a95a57eb4a5da895fcf80d1b1869
Source dataset
uspto-grants-1998_05
Patent number
US05750757

Reaction notes

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