Water → Methyl [2-(triphenylmethoxy)ethyl]carbamodithioate

HRID 1980369Notes

Reaction equation

HRID 1980369 reaction equation
[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][OH:7].[C:9]1([C:15](Cl)([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=2)[C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1.O>N1C=CC=CC=1>[CH3:1][S:2][C:3](=[S:8])[NH:4][CH2:5][CH2:6][O:7][C:15]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)([C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][CH:27]=1)[C:16]1[CH:17]=[CH:18][CH:19]=[CH:20][CH:21]=1

Participants

5

Reactant 3

HCID 962WaterHCID 6456Trityl chlorideHCID 13277332Methyl (2-hydroxyethyl)carbamodithioate

Product 1

HCID 54058214Methyl [2-(triphenylmethoxy)ethyl]carbamodithioateYield 75.5%

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Procedure

To a solution of N-(2-hydroxyethyl)dithiocarbamic acid methyl ester (7.5 g) in pyridine (40 ml) is added triphenylmethyl chloride (15 g), and the mixture is left to stand overnight at room temperature. The reaction mixture is poured into water and extracted with ethyl acetate. The extract is washed with diluted hydrochloric acid and water, dried and concentrated to remove the solvent. The residue is crystallized from a mixture of dichloromethane and ether to give N-(2-triphenylmethoxyethyl)dithiocarbamic acid methyl ester (14.73 g).

Workup

  1. waitthe mixture is left
  2. extractionextracted with ethyl acetate
  3. washThe extract is washed with diluted hydrochloric acid and water
  4. customdried
  5. concentrationconcentrated
  6. customto remove the solvent
  7. customThe residue is crystallized from a mixture of dichloromethane and ether

Sources & evidence

ORD record
ord-25d16449d4554ffea55143854dfd5ddc
Source dataset
uspto-grants-1985_04
Patent number
US04508909

Reaction notes

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