Benzene → HCID 12783508, compound

HRID 1577816Notes

Reaction equation

HRID 1577816 reaction equation
[CH2:1]([CH:3]1[NH:8][CH2:7][CH2:6][CH2:5][S:4]1)[CH3:2].[Cl:9][C:10]1[CH:11]=[C:12]([N:16]=[C:17]=[S:18])[CH:13]=[CH:14][CH:15]=1.C1C=CC=CC=1>CCCCCC>[Cl:9][C:10]1[CH:11]=[C:12]([NH:16][C:17]([N:8]2[CH2:7][CH2:6][CH2:5][S:4][CH:3]2[CH2:1][CH3:2])=[S:18])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 241BenzeneHCID 754493-Chlorophenyl isothiocyanateHCID 2550732-ethyl-1,3-thiazinane

Product 1

HCID 12783508HCID 12783508, compound

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 2.6 g. of 2-ethyltetrahydro-2H-1,3-thiazine, 3.4 g. of 3-chlorophenyl isothiocyanate, and 30 ml. of benzene was stirred, after an initial exotherm, at ambient temperature for about 64 hours. To the reaction mixture was added about 10 ml. of hexane, which caused white crystals to form. The mixture was cooled and filtered, and the solid was washed with hexane. The solid was recrystallized from about 500 ml. of 10:1 hexane:carbon tetrachloride to give N-(3-chlorophenyl)-2-ethyltetrahydro2H-1,3-thiazine-3-carbothioamide, m.p. 69°-73°. The following elemental microanalysis was obtained:

Workup

  1. additionA mixture of 2.6 g
  2. additionTo the reaction mixture was added about 10 ml
  3. customto form
  4. temperatureThe mixture was cooled
  5. filtrationfiltered
  6. washthe solid was washed with hexane
  7. customThe solid was recrystallized from about 500 ml

Sources & evidence

ORD record
ord-1311aa247f114affaf1e0eef5499ef7c
Source dataset
uspto-grants-1981_09
Patent number
US04289766

Reaction notes

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