Benzoyl isothiocyanate → HCID 118435603, compound

HRID 1487419Notes

Reaction equation

HRID 1487419 reaction equation
[C:1]([N:9]=[C:10]=[S:11])(=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[NH2:12][C@@:13]1([C:22]2[S:23][CH:24]=[C:25]([Br:27])[N:26]=2)[CH2:18][O:17][C@@H:16]([CH3:19])[CH2:15][C@H:14]1[CH2:20][OH:21]>ClCCl>[Br:27][C:25]1[N:26]=[C:22]([C@@:13]2([NH:12][C:10]([NH:9][C:1](=[O:8])[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[S:11])[C@H:14]([CH2:20][OH:21])[CH2:15][C@H:16]([CH3:19])[O:17][CH2:18]2)[S:23][CH:24]=1

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 118441539HCID 118441539, compound

Product 1

HCID 118435603HCID 118435603, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Benzoyl isothiocyanate (6.92 g, 42.4 mmol) was added in a drop-wise manner to a solution of C4 (14.48 g, 47.13 mmol) in dichloromethane (420 mL), and the reaction mixture was stirred at room temperature for 24 hours. Volatiles were removed in vacuo, and the residue was purified via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane), providing the product as a yellow solid. Yield: 14.7 g, 31.2 mmol, 66%. 1H NMR (400 MHz, CDCl3) δ 11.70 (br s, 1H), 8.93 (br s, 1H), 7.86-7.90 (m, 2H), 7.62-7.67 (m, 1H), 7.51-7.56 (m, 2H), 7.25 (s, 1H), 5.47 (d, J=11.9 Hz, 1H), 3.91 (d, J=12.0 Hz, 1H), 3.83 (d, J=4.4 Hz, 2H), 3.74-3.81 (m, 1H), 2.44-2.52 (m, 1H), 1.80-1.87 (m, 2H), 1.33 (d, J=6.2 Hz, 3H).

Workup

  1. customVolatiles were removed in vacuo
  2. customthe residue was purified via silica gel chromatography (Gradient: 0% to 50% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-4e68c42def3045699b6ea77cce316b4b
Source dataset
uspto-grants-2016_08
Patent number
US09428523B2

Reaction notes

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