Methoxycarbonyl isothiocyanate → HCID 4581444, compound

HRID 1733365Notes

Reaction equation

HRID 1733365 reaction equation
[N+:1]([C:4]1[CH:10]=[CH:9][C:8]([S:11][CH2:12][CH2:13][CH3:14])=[CH:7][C:5]=1[NH2:6])([O-:3])=[O:2].[C:15]([N:19]=[C:20]=[S:21])([O:17][CH3:18])=[O:16]>C(#N)C>[C:15]([NH:19][C:20](=[S:21])[NH:6][C:5]1[CH:7]=[C:8]([S:11][CH2:12][CH2:13][CH3:14])[CH:9]=[CH:10][C:4]=1[N+:1]([O-:3])=[O:2])([O:17][CH3:18])=[O:16]

Participants

4

Reactant 2

HCID 552246Methoxycarbonyl isothiocyanateHCID 643320Benzenamine, 2-nitro-5-(propylthio)-

Product 1

HCID 4581444HCID 4581444, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a stirred mixture of 2-nitro-5-propanylthioaniline (21.2 g.; 0.10 mole) in acetonitrile (50 ml.) is added portionwise carbomethoxy isothiocyanate (11.7 g.; 0.10 mole). The reaction mixture is maintained at room temperature and is filtered to remove a small amount of dark colored insoluble material. The clear filtrate was permitted to stand at room temperature for two hours and the precipitate which forms is collected by filtration, washed with cold acetonitrile and dried to yield 1-(3-carbomethoxythioureido)-2-nitro-5-propylthiobenzene (17.6 g.), m.p. 122°-125° C.

Workup

  1. filtrationis filtered
  2. customto remove a small amount of dark colored insoluble material
  3. filtrationthe precipitate which forms is collected by filtration
  4. washwashed with cold acetonitrile
  5. customdried

Sources & evidence

ORD record
ord-77b5391aaa7b48b2ba829c695b2d2ca2
Source dataset
uspto-grants-1980_12
Patent number
US04241079

Reaction notes

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