Water → 4-Chloro-2-fluoro-5-propargylthioaniline

HRID 580248

Reaction equation

HRID 580248 reaction equation
[NH2:1][C:2]1[C:3]([F:10])=[CH:4][C:5]([Cl:9])=[C:6]([SH:8])[CH:7]=1.[OH-].[Na+].O.[CH2:14](Cl)[C:15]#[CH:16]>[Cl-].C([N+](CCCC)(CCCC)CC1C=CC=CC=1)CCC.C(OCC)C>[Cl:9][C:5]1[C:6]([S:8][CH2:16][C:15]#[CH:14])=[CH:7][C:2]([NH2:1])=[C:3]([F:10])[CH:4]=1

Participants

7

Reactant 4

HCID 962WaterHCID 122213-Chloro-1-propyneHCID 14798Sodium HydroxideHCID 11019406Benzenethiol, 5-amino-2-chloro-4-fluoro-

Product 1

HCID 134889534-Chloro-2-fluoro-5-propargylthioanilineYield 31.9%

Reagents, catalysts & solvents 2

HCID 159952Benzyltributylammonium chlorideCatalystHCID 3283Diethyl EtherSolvent

Procedure

To a mixture of 5-amino-2-chloro-4-fluorothiophenol (8.4 g), sodium hydroxide (3 g), water (80 ml), diethyl ether (40 ml) and tributylbenzylammonium chloride (0.1 g), propargyl chloride (5.2 g) was dropwise added at room temperature (ca. 20° to 25° C.), and the resultant mixture was stirred at the same temperature for 3 hours. The water layer was separated and extracted with ether. The ether extract was combined with the ether layer, washed with water, dried and concentrated under reduced pressure. The residue was crystallized from methanol to give 3.25 g of 4-chloro-2-fluoro-5-propargylthioaniline. M.P., 58°-59.5° C.

Workup

  1. additionwas dropwise added at room temperature (ca. 20° to 25° C.)
  2. customThe water layer was separated
  3. extractionextracted with ether
  4. extractionThe ether extract
  5. washwashed with water
  6. customdried
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from methanol

Sources & evidence

ORD record
ord-2c33be2925fe41ca9099c2546e231f2c
Source dataset
uspto-grants-1988_06
Patent number
US04752325

Linked notes

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