Methanethiol → Methyl benzoyldithiocarbamate

HRID 2309336Notes

Reaction equation

HRID 2309336 reaction equation
[N+]([C:4]1[CH:12]=[CH:11][CH:10]=[CH:9][C:5]=1[C:6](Cl)=[O:7])([O-])=O.[S-:13]C#N.[K+].[C:17]([S:25][C:26]#[N:27])(=O)C1C=CC=CC=1.CS>C(O)C.CO.C1(C)C=CC=CC=1>[C:6]([NH:27][C:26](=[S:13])[S:25][CH3:17])(=[O:7])[C:5]1[CH:9]=[CH:10][CH:11]=[CH:12][CH:4]=1

Participants

8

Reactant 4

HCID 878MethanethiolHCID 118752-Nitrobenzoyl chlorideHCID 516872Potassium thiocyanateHCID 13203561Benzoyl thiocyanate

Product 1

HCID 12497894Methyl benzoyldithiocarbamate

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 887MethanolSolventHCID 1140TolueneSolvent

Procedure

Thus, in the reaction of Equation 43a, 2-nitrobenzoyl chloride LVII is reacted with potassium thiocyanate in a solvent such as toluene or acetronitrile at reflux for 0.2 to 5 hours; the resultant benzoyl thiocyanate is then reacted with excess methanol, ethanol or methyl mercaptan at 25° to 80° C. for 0.2 to 5 hours to form an O-alkyl benzoylthiocarbamate or methyl benzoyldithiocarbamate of Formula (LVIII). In reaction 43b, LVIII is reacted with sodium methoxide and methyl iodide in methanol at 0° to 25° C. for 1 to 5 hours to form a dialkyl benzoyliminothiocarbonate or dimethyl benzoyliminodithiocarbonate of Formula (LIX). And in reaction 43c, LIX is reacted with hydroxylamine in methanol or ethanol at 0° to 25° C. for about 10 to 96 hours to form Xm'.

Workup

  1. temperatureat reflux for 0.2 to 5 hours

Sources & evidence

ORD record
ord-2253f9b5ce784b2595b82e9ae1beb076
Source dataset
uspto-grants-1987_09
Patent number
US04695311

Reaction notes

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