m-Tolyl isocyanate → HCID 15670968, compound

HRID 1769720Notes

Reaction equation

HRID 1769720 reaction equation
[CH3:1][C:2]1[CH:3]=[C:4]([N:8]=[C:9]=[O:10])[CH:5]=[CH:6][CH:7]=1.[NH2:11][CH2:12][C:13]([N:15]([CH2:22][C:23]([N:25]1[CH2:34][CH2:33][C:28]2([CH2:32][CH2:31][CH2:30][CH2:29]2)[CH2:27][CH2:26]1)=[O:24])[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:14]>O1CCCC1>[CH2:29]1[C:28]2([CH2:33][CH2:34][N:25]([C:23](=[O:24])[CH2:22][N:15]([C:16]3[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=3)[C:13](=[O:14])[CH2:12][NH:11][C:9]([NH:8][C:4]3[CH:5]=[CH:6][CH:7]=[C:2]([CH3:1])[CH:3]=3)=[O:10])[CH2:26][CH2:27]2)[CH2:32][CH2:31][CH2:30]1

Participants

4

Reactant 2

HCID 69303m-Tolyl isocyanateHCID 15670967HCID 15670967, compound

Product 1

HCID 15670968HCID 15670968, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.49 g of 3-methylphenyl isocyanate is added at a temperature close to 25° C to a solution of 1.2 g of 2-amino-N-[2-(8-azaspiro[4,5]decan-8-yl)-2-oxoethyl]-N-phenylacetamide in 50 cm3 of anhydrous tetrahydrofuran. The mixture is stirred for 12 hours at a temperature close to 25° C and the insoluble product is separated off by filtration. After recrystallization from ethyl acetate, 0.7 g of N-[2-(8azaspiro[4,5]decan-8-yl)-2-oxoethyl]-2-[3-(3-methylphenyl)ureido]-N-phenylacetamide melting at 183° C. is obtained.

Workup

  1. customclose to 25° C
  2. customthe insoluble product is separated off by filtration
  3. customAfter recrystallization from ethyl acetate

Sources & evidence

ORD record
ord-2299a4f20f274af9b297b5c7212916d9
Source dataset
uspto-grants-1995_01
Patent number
US05382590

Reaction notes

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