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

HRID 1408810Notes

Reaction equation

HRID 1408810 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-57fb93ad33b44c8db3fe8581cab45eb8
Source dataset
uspto-grants-2014_12
Patent number
US08921359B2

Reaction notes

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