Methanethiol → Benzenecarbodithioic acid, 4-amino-, methyl ester

HRID 1658678Notes

Reaction equation

HRID 1658678 reaction equation
CS.[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([C:10]([S:12][CH2:13]C(O)=O)=[S:11])=[CH:6][CH:5]=1.C(=O)(O)[O-].[Na+]>[OH-].[Na+]>[NH2:3][C:4]1[CH:5]=[CH:6][C:7]([C:10]([S:12][CH3:13])=[S:11])=[CH:8][CH:9]=1

Participants

5

Reactant 3

HCID 878MethanethiolHCID 516892Sodium BicarbonateHCID 54194572HCID 54194572, compound

Product 1

HCID 162765Benzenecarbodithioic acid, 4-amino-, methyl ester

Reagents, catalysts & solvents 1

HCID 14798Sodium HydroxideSolvent

Procedure

Methyl mercaptan was passed into a filtered solution of crude carboxymethyl 4-aminobenzenecarbodithioate (7.48 g, 0.033 mol)in 66 ml of 0.5 N of sodium hydroxide solution containing 10% by weight sodium bicarbonate under external ice-cooling for about 10 minutes. A yellow precipitate separated out gradually as the colour of the aqueous solution was discharged. After standing for 1 hour at 0°-5°C, the precipitate was filtered off, washed with 10% by weight sodium bicarbonate solution, then with water and dried in vacuo at a temperature of below 50°C. The yield of the yellow crystalline powder, m.p. 74.5°-75.5° (decomp.) was 5.3 g or 87.7%.

Workup

  1. temperaturecooling for about 10 minutes
  2. customA yellow precipitate separated out gradually as the colour of the aqueous solution
  3. filtrationthe precipitate was filtered off
  4. washwashed with 10% by weight sodium bicarbonate solution
  5. dry with materialwith water and dried in vacuo at a temperature of below 50°C

Sources & evidence

ORD record
ord-3abe7234e88148909ecf189be43a7653
Source dataset
uspto-grants-1976_06
Patent number
US03966397

Reaction notes

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