Methanethiol → HCID 12275462, compound

HRID 649268Notes

Reaction equation

HRID 649268 reaction equation
[NH2:1][C:2]1[C:3](OP(N2CCOCC2)(N2CCOCC2)=O)=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:9][C:8]([Cl:18])=[CH:7][CH:6]=2.[Na].[CH3:35][SH:36]>O1CCCC1>[NH2:1][C:2]1[C:3]([S:36][CH3:35])=[N:4][C:5]2[C:10]([C:11]=1[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[CH:9][C:8]([Cl:18])=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 878MethanethiolHCID 5360545SodiumHCID 20142992HCID 20142992, compound

Product 1

HCID 12275462HCID 12275462, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of 488.9 mg (1.0 mmole) of 3-amino-6-chloro-2-(dimorpholino)phosphinyloxy-4-phenylquinoline in 30 ml of dry tetrahydrofuran was added 4 ml of a 1M solution of sodium salt of methyl mercaptan in cellusolve. The reaction mixture was heated to reflux for 2 hrs. The resulting suspension was then allowed to cool to room temperature at which time the insoluble salts were removed by filtration. The filtrate was concentrated to an oily gum. The gum was separated by preparative thin-layer chromatography (six 20 cm×20 cm×1.5 mm silica gel plates developed in a 1:9 (v/v) mixture of ether and benzene. The desired product was isolated and crystallized from ether-hexane. The product consisted of light yellow prisms were collected, mp 115°-117°. This material was found to be identical to that of an authentic sample (mp 115°-117°) by tlc and mixture mp.

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 2 hrs
  3. customwere removed by filtration
  4. concentrationThe filtrate was concentrated to an oily gum
  5. customThe gum was separated by preparative thin-layer chromatography (six 20 cm×20 cm×1.5 mm silica gel plates
  6. additiondeveloped in a 1:9 (v/v) mixture of ether and benzene

Sources & evidence

ORD record
ord-4de453e299794b418b6b4e1544d1be2d
Source dataset
uspto-grants-1988_04
Patent number
US04739049

Reaction notes

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