Phenyl Isothiocyanate → HCID 15462641, compound

HRID 1003215Notes

Reaction equation

HRID 1003215 reaction equation
[CH2:1]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][NH:16][CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:4][CH3:5])[CH3:2].[C:35]1([N:41]=[C:42]=[S:43])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>O1CCCC1>[CH2:4]([N:3]([CH2:6][C:7]1[N:12]=[C:11]2[S:13][C:14]3[CH2:15][N:16]([C:42](=[S:43])[NH:41][C:35]4[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=4)[CH2:17][CH2:18][C:19]=3[C:10]2=[C:9]([C:20]2[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[C:22]([O:28][CH3:29])[CH:21]=2)[C:8]=1[C:30]([O:32][CH2:33][CH3:34])=[O:31])[CH2:1][CH3:2])[CH3:5]

Participants

4

Reactant 2

HCID 7673Phenyl IsothiocyanateHCID 10505011HCID 10505011, compound

Product 1

HCID 15462641HCID 15462641, compoundYield 80.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound obtained in Example 5A (1.0 g), phenyl isothiocyanate (0.31 g) and tetrahydrofuran (20 ml) was stirred at room temperature for 14 hours, after which it was concentrated under reduced pressure. The residue was subjected to silica gel column chromatography and eluted with ethyl acetate-hexane-methanol (20:20:1, v/v) to yield ethyl 2-(N,N-diethylaminomethyl)-4-(3,4-dimethoxyphenyl)-7-phenylthiocarbamoyl-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (1.03 g, 80%), which was then recrystallized from ethyl acetate-hexane to yield colorless crystals having a melting point of 104 to 106° C. ##STR51##

Workup

  1. concentrationafter which it was concentrated under reduced pressure
  2. washeluted with ethyl acetate-hexane-methanol (20:20:1

Sources & evidence

ORD record
ord-013dde93776d486bafe70b50f8125528
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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