Phosphorus oxychloride → HCID 178420221, compound

HRID 710543Notes

Reaction equation

HRID 710543 reaction equation
Cl.[NH2:2][CH2:3][C:4](=O)[CH2:5][CH2:6][C:7]1[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.[N:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23](O)=O)=[CH:22][C:17]=2[NH:16][CH:15]=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:35])=CC=1.O=P(Cl)(Cl)Cl>>[NH:14]1[C:18]2[CH:19]=[CH:20][C:21]([C:23]3[S:35][C:4]([CH2:5][CH2:6][C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[CH:3][N:2]=3)=[CH:22][C:17]=2[N:16]=[CH:15]1

Participants

5

Reactant 4

HCID 24813Phosphorus oxychlorideHCID 87949Lawesson's reagentHCID 4594565-Benzimidazolecarboxylic acidHCID 1329067831419-53-1

Product 1

HCID 178420221HCID 178420221, compound

Procedure

The compound was synthesized starting from amino-4-phenylbutan-2-on-hydrochloride (163 mg; 1 mmol), benzimidazol-5-carboxylic acid (248 mg; 1 mmol), Lawesson's reagent (606 mg; 1.5 mmol), TEA (0.22 ml, 0.3 mmol) and POCl3 (0.137 ml; 1.5 mmol) as described above; yield: 0.042 g (13.8%); MS m/z: 306.1 [M+H]+; 1H-NMR (DMSO d6, 400 MHz): δ 2.98 (t, 2H, 3J=7.5 Hz); 3.20 (t, 2H, 3J=7.5 Hz); 7.17-7.22 (m, 1H); 7.25-7.31 (m, 4H); 7.62 (s, 1H); 7.80 (d, 1H, 3J=8.7 Hz); 7.90 (dd, 1H, 4J=1.7 Hz, 3J=8.3 Hz); 8.16 (d, 1H, 4J=1.7 Hz); 9.02 (s, 1H); HPLC (METHOD [A]): rt 13.73 min (97.4%)

Workup

  1. customThe compound was synthesized
  2. customrt 13.73 min (97.4%)

Sources & evidence

ORD record
ord-9945d24cb5fd4ab49b9b9467bdd5b09a
Source dataset
uspto-grants-2015_11
Patent number
US09181233B2

Reaction notes

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