Carbon Disulfide → Carbamodithioic acid, bis(phenylmethyl)-, sodium salt

HRID 1105881Notes

Reaction equation

HRID 1105881 reaction equation
[OH-].[Na+:2].[CH2:3]([NH:10][CH2:11][C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)[C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1.[C:18](=[S:20])=[S:19]>O>[Na+:2].[CH2:11]([N:10]([CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][CH:5]=1)[C:18](=[S:19])[S-:20])[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1

Participants

5

Reactant 3

HCID 6348Carbon DisulfideHCID 7656DibenzylamineHCID 14798Sodium Hydroxide

Product 1

HCID 4676203Carbamodithioic acid, bis(phenylmethyl)-, sodium saltYield 74%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

To a solution of 8.0 g. (0.2 mole) of sodium hydroxide in 32 ml of water was added 39.4 g. (0.2 mole) of dibenzyl amine. The mixture was cooled to 0° and to it was added 25.3 g. (0.334 mole) of carbon disulfide. A solid separated spontaneously. The mixture was stirred at room temperature for 1 hour, and then filtered. The solid was triturated first with 100 ml of ether and then with 100 ml of benzene and dried to give 43.5 g. (74% yield) of N,N-dibenzyldithiocarbamic acid sodium salt, mp 260°.

Workup

  1. temperatureThe mixture was cooled to 0° and to it
  2. additionwas added 25.3 g
  3. customA solid separated spontaneously
  4. filtrationfiltered
  5. customThe solid was triturated first with 100 ml of ether
  6. dry with materialwith 100 ml of benzene and dried
  7. customto give 43.5 g

Sources & evidence

ORD record
ord-4a76c47614e54a7a98d9e03dbe51a3ff
Source dataset
uspto-grants-1982_01
Patent number
US04310590

Reaction notes

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