Methyl Isocyanate → HCID 20396812, compound

HRID 972024Notes

Reaction equation

HRID 972024 reaction equation
[OH:1][CH:2]([CH2:41][N:42]1[C:46](=[O:47])[C:45]2([CH2:52][C:51]([CH3:54])([CH3:53])[NH:50][C:49]([CH3:56])([CH3:55])[CH2:48]2)[NH:44][C:43]1=[O:57])[CH2:3][O:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([C:14]2[CH:19]=[CH:18][C:17]([O:20][CH2:21][CH:22]([OH:40])[CH2:23][N:24]3[C:28](=[O:29])[C:27]4([CH2:34][C:33]([CH3:36])([CH3:35])[NH:32][C:31]([CH3:38])([CH3:37])[CH2:30]4)[NH:26][C:25]3=[O:39])=[CH:16][CH:15]=2)([CH3:13])[CH3:12])=[CH:7][CH:6]=1.[CH3:58][N:59]=[C:60]=[O:61]>>[CH3:58][NH:59][C:60]([O:40][CH:22]([CH2:23][N:24]1[C:28](=[O:29])[C:27]2([CH2:34][C:33]([CH3:35])([CH3:36])[NH:32][C:31]([CH3:37])([CH3:38])[CH2:30]2)[NH:26][C:25]1=[O:39])[CH2:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([C:11]([C:8]2[CH:7]=[CH:6][C:5]([O:4][CH2:3][CH:2]([O:1][C:25](=[O:39])[NH:24][CH3:23])[CH2:41][N:42]3[C:46](=[O:47])[C:45]4([CH2:48][C:49]([CH3:56])([CH3:55])[NH:50][C:51]([CH3:54])([CH3:53])[CH2:52]4)[NH:44][C:43]3=[O:57])=[CH:10][CH:9]=2)([CH3:13])[CH3:12])=[CH:15][CH:16]=1)=[O:61]

Participants

3

Reactant 2

HCID 12228Methyl Isocyanate2×HCID 234627182,2-Bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane

Product 1

HCID 20396812HCID 20396812, compound

Procedure

A mixture of 5.0 g of 2,2-bis{4-[2-hydroxy-3-(7,7,9,9-tetramethyl-2,4-dioxo-1,3,8-triazaspiro[4.5]dec-3-yl)propoxy]phenyl}propane (prepared as described in Example 2) and 25.0 g of methyl isocyanate was refluxed for 8.5 hours. After completion of the reaction, excess methyl isocyanate was evaporated from the reaction mixture and then the residue was purified by column chromatography through silica gel eluted with a 24:12:2:1 by volume mixture of ethyl acetate, benzene, triethylamine and ethanol and then by recrystallisation from ethanol. The desired Compound No. 31 was obtained in the form of white crystals, melting point 238°-242° C.

Workup

  1. temperaturewas refluxed for 8.5 hours
  2. customwas evaporated from the reaction mixture
  3. customthe residue was purified by column chromatography through silica gel
  4. washeluted with a 24:12:2:1 by volume mixture of ethyl acetate, benzene, triethylamine and ethanol
  5. customby recrystallisation from ethanol
  6. custom31 was obtained in the form of white crystals, melting point 238°-242° C.

Sources & evidence

ORD record
ord-40fe96a0f1fd4737b240263bef95ee68
Source dataset
uspto-grants-1979_07
Patent number
US04162246

Reaction notes

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