Sodium Hydroxide → 855531-19-0

HRID 2222197Notes

Reaction equation

HRID 2222197 reaction equation
[N:1]([C:4]1(Cl)[CH:9]=[CH:8][CH:7]=[CH:6][CH2:5]1)=[C:2]=[S:3].[ClH:11].[CH:12]([NH2:14])=[NH:13].[OH-].[Na+]>C1COCC1>[NH2:13][CH:12]=[N:14][C:2]([NH:1][C:4]1[CH:9]=[CH:8][C:7]([Cl:11])=[CH:6][CH:5]=1)=[S:3]

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 10313058Methanimidamide, hydrochloride (1:1)HCID 86599617HCID 86599617, compound

Product 1

HCID 86056609855531-19-0

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 10 g (51.2 mmol) 4-isothiocyanato-4-chloro benzene in 51 ml THF at 0° C. was treated with 5.15 g (64.02 mmol) formamidine hydrochloride and 64 ml 1N NaOH and allowed to stirr for 5 h after which the mixture was concentrated. 500 ml ethyl acetate and 100 ml water was added and the precipitate was filtered off, washed with water and dried to yield the intermediate 1-[1-Amino-methylidene]-3-(4-chloro-phenyl)-thiourea (MH+ 213.5) which was used without further purification. The thiourea was taken up in 50 ml THF and treated with 8.55 g (51.2 mmol) ethyl bromoacetate and 15.3 ml NEt3 and stirred at 50° C. for 18 h. The mixture was concentrated and extracted with CHCl3. The organic layer was washed with aqueous Na2CO3 (1M) and saturated NaCl solution, dried with MgSO4 and evaporated. The residue was purified with column chromatography on silica to yield 3.48 g (22%) of the title compound.

Workup

  1. concentrationafter which the mixture was concentrated
  2. addition500 ml ethyl acetate and 100 ml water was added
  3. filtrationthe precipitate was filtered off
  4. washwashed with water
  5. customdried

Sources & evidence

ORD record
ord-f5f4ba0f64c745feb977bb0ce40c3326
Source dataset
uspto-grants-2008_05
Patent number
US07371751B2

Reaction notes

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