Methyl Isocyanate → HCID 15462642, compound

HRID 1003217Notes

Reaction equation

HRID 1003217 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].[CH3:35][N:36]=[C:37]=[O:38]>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:37](=[O:38])[NH:36][CH3:35])[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 12228Methyl IsocyanateHCID 10505011HCID 10505011, compound

Product 1

HCID 15462642HCID 15462642, compoundYield 22%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of the compound obtained in Example 5A (1.22 g), methyl isocyanate (0.17 g) and tetrahydrofuran (20 ml) was stirred at room temperature for 5 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-methylcarbamoyl-5,6,7,8-tetrahydrothieno[2,3-b:5,4-c']dipyridine-3-carboxylate (for structural formula, see below), (0.30 g, 22%), which was then recrystallized from ethyl acetate-hexane to yield colorless prismatic crystals having a melting point of 153 to 155° C. ##STR53##

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-b970bba908fb4e03be8baef95c65fdda
Source dataset
uspto-grants-2000_04
Patent number
US06046189

Reaction notes

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