Benzyl isocyanate → HCID 58941220, compound

HRID 747623Notes

Reaction equation

HRID 747623 reaction equation
[NH2:1][CH2:2][CH2:3][N:4]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH2:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1[F:33])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)(=[O:7])=[O:6].[CH2:34]([N:41]=[C:42]=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH2:34]([NH:41][C:42]([NH:1][CH2:2][CH2:3][N:4]([C:18]1[CH:23]=[CH:22][C:21]([CH3:24])=[CH:20][C:19]=1[CH2:25][C:26]1[C:31]([F:32])=[CH:30][CH:29]=[CH:28][C:27]=1[F:33])[S:5]([C:8]1[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[C:10]([O:16][CH3:17])[CH:9]=1)(=[O:6])=[O:7])=[O:43])[C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

4

Reactant 2

HCID 76639Benzyl isocyanateHCID 58941371HCID 58941371, compound2×

Product 1

HCID 58941220HCID 58941220, compoundYield 53.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To 1 g of N-(2-aminoethyl)-N-[2-(2,6-difluorobenzyl)-4-methylphenyl]-3,4-dimethoxybenzenesulfonamide (compound 215) dissolved in 20 ml of THF is added 0.266 g of benzyl isocyanate, and, after refluxing for 3 hours, the medium is evaporated to dryness. The residue is chromatographed on a column of silica gel, eluting with an 8/2 (v/v) toluene/ethyl acetate mixture to give 0.65 g of the expected product.

Workup

  1. temperatureafter refluxing for 3 hours
  2. customthe medium is evaporated to dryness
  3. customThe residue is chromatographed on a column of silica gel
  4. washeluting with an 8/2 (v/v) toluene/ethyl acetate mixture

Sources & evidence

ORD record
ord-490bd13e80e54f7fbda12d365441a6b2
Source dataset
uspto-grants-2008_07
Patent number
US07396958B2

Reaction notes

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