Methanethiol → HCID 86735489, compound

HRID 616729Notes

Reaction equation

HRID 616729 reaction equation
C[SH:2].[H-].[Na+].[CH3:5][C:6]([CH:8]([N:10]([C:19](=O)CCl)[C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:9])=[S:7].Cl[CH2:24][C:25](Cl)=O>O1CCCC1.C(OCC)C>[CH3:5][C:6]([CH:8]([N:10]([C:19](=[S:2])[CH2:24][CH3:25])[C:11]1[C:16]([CH3:17])=[CH:15][CH:14]=[CH:13][C:12]=1[CH3:18])[CH3:9])=[S:7]

Participants

7

Reactant 4

HCID 878MethanethiolHCID 6577Chloroacetyl chlorideHCID 24758Sodium hydrideHCID 20368964HCID 20368964, compound

Product 1

HCID 86735489HCID 86735489, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent2×

Procedure

While passing in nitrogen and stirring, 3.1 g of methyl mercaptan are introduced into a suspension of 2.8 g of 55% sodium hydride in 150 ml of tetrahydrofurane and subsequently 18 g of N-(1'-methylthiocarbonylethyl)-N-chloroacetyl-2,6-dimethylaniline (prepared by chloroacetylating the intermediate obtained in Example 1a) with, for example, chloroacetyl chloride) in 50 ml of tetrahydrofurane were added dropwise. Stirring was continued for 48 hours at room temperature and the reaction mixture was diluted with 300 ml of diethyl ether, washed three times with water, dried over sodium sulphate and filtered. After recrystallisation from diethyl ether/petroleum ether, compound 2 had a melting point of 88°-92° C.

Workup

  1. customprepared
  2. additionwere added dropwise
  3. stirringStirring
  4. washwashed three times with water
  5. dry with materialdried over sodium sulphate
  6. filtrationfiltered
  7. customAfter recrystallisation from diethyl ether/petroleum ether, compound 2

Sources & evidence

ORD record
ord-93681fb942944703a5462ca570c19f89
Source dataset
uspto-grants-1978_02
Patent number
US04075349

Reaction notes

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