Phenyl isocyanate → HCID 10555594, compound

HRID 1003216Notes

Reaction equation

HRID 1003216 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]=[O: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](=[O: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 7672Phenyl isocyanateHCID 10505011HCID 10505011, compound

Product 1

HCID 10555594HCID 10555594, compoundYield 88.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound obtained in Example 5A (1.0 g), phenyl isocyanate (0.27 g) and tetrahydrofuran (20 ml) was stirred at room temperature for 3 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-phenylcarbamoyl-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below) (1.10 g, 88%), which was then recrystallized from ethyl acetate-hexane to yield colorless prismatic crystals having a melting point of 154 to 155° C. ##STR52##

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-07883b71a0ff463ca01aa64a04b91c8c
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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