Water → 4-(3-Chloropropoxy)benzenecarbothioamide

HRID 1710746Notes

Reaction equation

HRID 1710746 reaction equation
[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10]([NH2:12])=O)=[CH:8][CH:7]=1.COC1C=CC(P2(=S)SP(=S)(C3C=CC(OC)=CC=3)[S:24]2)=CC=1.O>C(Cl)(Cl)Cl.C1(C)C=CC=CC=1>[Cl:1][CH2:2][CH2:3][CH2:4][O:5][C:6]1[CH:14]=[CH:13][C:9]([C:10](=[S:24])[NH2:12])=[CH:8][CH:7]=1

Participants

6

Reactant 3

HCID 962WaterHCID 87949Lawesson's reagentHCID 144071764-(3-Chloropropoxy)benzamide

Product 1

HCID 594574624-(3-Chloropropoxy)benzenecarbothioamideYield 85%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6212ChloroformSolvent

Conditions

Temperature
85 °C

Procedure

4-(3-Chloropropoxy)benzamide ax54 (1.0 g, 4.6 mmole, 1 eq) is dissolved in a 1:1 mixture of chloroform and toluene, 2,4-bis-(4-methoxyphenyl)-1,3-dithia-2,4-diphosphetane-2,4-disulfide (1.5 g, 3.7 mmole, 0.8 eq) is added. The reaction is stirred overnight at 85° C. Water is then added and the phases are separated. The organic layer is dried over magnesium sulfate and concentrated under reduce pressure. The crude material is purified by chromatography on silicagel (eluent: dichloromethane/methanol/ammonia 98:1.8:0.2) to provide 0.91 g of 4-(3-chloropropoxy)benzenecarbothioamide ax71 as a white solid.

Workup

  1. additionis added
  2. customthe phases are separated
  3. dry with materialThe organic layer is dried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe crude material is purified by chromatography on silicagel (eluent: dichloromethane/methanol/ammonia 98:1.8:0.2)

Sources & evidence

ORD record
ord-2904dfb7cc07414faefca94bc5892ed2
Source dataset
uspto-grants-2010_09
Patent number
US07790720B2

Reaction notes

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