Benzoyl isothiocyanate → HCID 57633985, compound

HRID 2109732Notes

Reaction equation

HRID 2109732 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.Cl.Cl.[Cl:14][C:15]1[CH:20]=[CH:19][C:18]([CH2:21][C@H:22]([NH2:25])[CH2:23][NH2:24])=[CH:17][CH:16]=1>C(Cl)Cl>[NH2:25][C@@H:22]([CH2:21][C:18]1[CH:17]=[CH:16][C:15]([Cl:14])=[CH:20][CH:19]=1)[CH2:23][NH:24][C:10]([NH:9][C:1](=[O:8])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1)=[S:11]

Participants

4

Reactant 2

HCID 68284Benzoyl isothiocyanateHCID 68989979HCID 68989979, compound

Product 1

HCID 57633985HCID 57633985, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of benzoyl isothiocyanate (2.94 mL, 21.9 mmol) in DCM (50 mL) was added dropwise via an addition funnel to the mixture of (S)-3-(4-chlorophenyl)propane-1,2-diamine dihydrochloride (5.63 g, 21.9 mmol) and TEA (7.60 mL, 54.6 mmol) in DCM (200 mL) at −10° C. under nitrogen. The addition took 30 minutes. The mixture was then gradually warmed to ambient temperature and stirred overnight. The solvent was removed in vacuo. The residue was partitioned between EtOAc and water. The combined organic portions were washed with brine. The crude product was purified by flash column chromatography (20 to 100% of EtOAc in hexanes, Biotage Si 40M). The product was obtained as an off-white foamy solid, 5.53 g, 73%. 1H NMR (300 MHz, CDCl3) δ 1.84 (broad, NH2), 2.57-2.71 (m, 1H), 2.82-2.94 (m, 1H), 3.34-3.48 (m, 1H), 3.51-3.65 (m, 1H), 3.82-3.99 (m, 1H), 7.13-7.21 (m, 2H), 7.28-7.34 (m, 2H), 7.49-7.58 (m, 2H), 7.59-7.68 (m, 1H), 7.80-7.91 (m, 2H), 9.00 (broad, NH), 11.07 (broad, NH). LCMS (API-ES): 348.1/350.1 (M++H), chloro pattern.

Workup

  1. additionThe addition
  2. customThe solvent was removed in vacuo
  3. customThe residue was partitioned between EtOAc and water
  4. washThe combined organic portions were washed with brine
  5. customThe crude product was purified by flash column chromatography (20 to 100% of EtOAc in hexanes, Biotage Si 40M)
  6. customThe product was obtained as an off-white foamy solid, 5.53 g, 73%

Sources & evidence

ORD record
ord-e95523dc88224d069905d172924b0a51
Source dataset
uspto-grants-2009_04
Patent number
US07514566B2

Reaction notes

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