Methane → HCID 20472817, compound

HRID 2296382Notes

Reaction equation

HRID 2296382 reaction equation
[NH:1]=[C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[S:3]1.[OH-:11].[Na+].[CH4:13]>C(O)CO>[CH3:13][N:6]([C:5]1[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=1[SH:3])[C:2]([NH2:1])=[O:11]

Participants

5

Reactant 3

HCID 297MethaneHCID 14798Sodium HydroxideHCID 178509080HCID 178509080, compound

Product 1

HCID 20472817HCID 20472817, compoundYield 90.9%

Reagents, catalysts & solvents 1

HCID 174Ethylene GlycolSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 164 parts of 2-iminobenzothiazoline, 150 parts of sodium hydroxide and 300 parts of ethyleneglycol is stirred for 6 hours at 130°-140° C., subsequently cooled to 80° C., and introduced with agitation into 3000 parts of icewater. After further agitation for 30 minutes, 5 parts of active charcoal are added, the solution is stirred for a further 15 minutes and then filtered. The pH of the filtrate is adjusted to 5-6 by means of 10% aqueous hydrochloric acid, and the precipitated N-methyl-N-(2-mercaptophenyl)-urea is isolated by filtration. The moist product is immediately introduced into 700 parts of a 10% aqueous hydrochloric acid and heated for 15 minutes with agitation at 90° C. The precipitating 3-methyl-2(3H)-benzothiazolone of the formula ##STR4## is isolated by filtration after cooling the acidic batch, washed with water and dried. 150 Parts of an analytically pure product are obtained; this corresponds to a yield of 90.9% of theory, relative to 2-iminobenzothiazoline, melting point 73°-75° C.

Workup

  1. additionintroduced with agitation into 3000 parts of icewater
  2. waitAfter further agitation for 30 minutes
  3. stirringthe solution is stirred for a further 15 minutes
  4. filtrationfiltered

Sources & evidence

ORD record
ord-ba30a439df0d4470b0f23eb673c5d6c1
Source dataset
uspto-grants-1984_01
Patent number
US04429134

Reaction notes

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