1-Tert-butyl-4-isocyanatobenzene → HCID 68455943, compound

HRID 2358437Notes

Reaction equation

[NH2:1][CH:2]([C:4]1[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[CH:5]=1)[CH3:3].[C:23]([C:27]1[CH:32]=[CH:31][C:30]([N:33]=[C:34]=[O:35])=[CH:29][CH:28]=1)([CH3:26])([CH3:25])[CH3:24]>C(Cl)Cl>[C:23]([C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:34](=[O:35])[NH:1][CH:2]([C:4]2[CH:9]=[CH:8][C:7]([NH:10][S:11]([CH3:14])(=[O:13])=[O:12])=[C:6]([C:15]#[C:16][C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][CH:22]=3)[CH:5]=2)[CH3:3])=[CH:29][CH:28]=1)([CH3:26])([CH3:24])[CH3:25]

Participants

Conditions

Temperature: 0 °C

Procedure

N-[4-(1-Aminoethyl)-2-phenylethynylphenyl]methanesulfonamide (440.1 mg, 1.40 mmol) and TEA (390.3 μl, 2.800 mmol, 2 eq) were added in methylene chloride. The reaction mixture was cooled down to 0° C. 4-tert-Butylphenyl isocyanate (248.8%, 1.540 mmol, 1.3 eq.) was added into the mixture. The reaction mixture was stirred for 1 hr. Methylene chloride was removed in vacuo. The residue was purified with column chromatography (n-Hx:EA=2:1) to yield title compound (241.4 mg, 35%) as a solid.

Workup

customMethylene chloride was removed in vacuo
customThe residue was purified with column chromatography (n-Hx:EA=2:1)

Sources & evidence

ORD record: ord-37fb83939d464209a45ea163f6bb678f
Source dataset: uspto-grants-2010_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07763657B2

Reaction notes

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