Tert-Butylamine → 3-(2'-(tert-butylamino)-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzonitrile

HRID 2096622Notes

Reaction equation

HRID 2096622 reaction equation
[C:1]([NH2:5])([CH3:4])([CH3:3])[CH3:2].I[CH2:7][C:8]1([N:32]=[C:33]=[S:34])[C:17]2[C:12](=[CH:13][CH:14]=[C:15]([C:18]3[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=3)[C:21]#[N:22])[CH:16]=2)[O:11][CH:10]([C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH2:9]1>C(Cl)(Cl)Cl>[C:1]([NH:5][C:33]1[S:34][CH2:7][C:8]2([C:17]3[C:12](=[CH:13][CH:14]=[C:15]([C:18]4[CH:19]=[C:20]([CH:23]=[CH:24][CH:25]=4)[C:21]#[N:22])[CH:16]=3)[O:11][CH:10]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[CH2:9]2)[N:32]=1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 6385Tert-ButylamineHCID 866574513-(4-Iodomethyl-4-isothiocyanato-2-phenyl-chroman-6-yl)-benzonitrile

Product 1

HCID 671746273-(2'-(tert-butylamino)-2-phenyl-5'H-spiro[chroman-4,4'-thiazole]-6-yl)benzonitrileYield 21%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

t-BuNH2 (55 mg, 0.75 mmol) was added to 3-(4-iodomethyl-4-isothiocyanato-2-phenyl-chroman-6-yl)-benzonitrile (190.5 mg, 0.375 mmol) in CHCl3 above and the mixture was stirred for 20 minutes. The solvent was removed in vacuo to give the residue, which was purified by preparative TLC to give 3-(2′-(tert-butylamino)-2-phenyl-5′H-spiro[chroman-4,4′-thiazole]-6-yl)benzonitrile (35 mg, 21%).

Workup

  1. customThe solvent was removed in vacuo
  2. customto give the residue, which
  3. customwas purified by preparative TLC

Sources & evidence

ORD record
ord-48b576c552e8479dbf5cfbec250b8807
Source dataset
uspto-grants-2013_05
Patent number
US08450308B2

Reaction notes

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