Phosphorus oxychloride → HCID 67220084, compound

HRID 983897Notes

Reaction equation

[NH2:1][C:2]1[CH:15]=[C:14]([O:16][CH3:17])[CH:13]=[CH:12][C:3]=1[C:4]([C:6]1C=CC=CC=1)=[O:5].[CH:18]([C:21]1[N:22]=[C:23]([C:26](O)=[O:27])[S:24][CH:25]=1)(C)C.O=P(Cl)(Cl)Cl>N1C=CC=CC=1>[C:4]([C:3]1[CH:12]=[CH:13][C:14]([O:16][CH3:17])=[CH:15][C:2]=1[NH:1][C:26]([C:23]1[S:24][CH:25]=[C:21]([CH3:18])[N:22]=1)=[O:27])(=[O:5])[CH3:6]

Participants

Conditions

Temperature: -30 °C

Procedure

Step E) To a suspension of 2.59 g (15.7 mmol) of 2-amino-4-methoxybenzophenone (product of step D) and 2.68 g (15.7 mmol) of 4-isopropylthiazole-2-carboxylic acid (product of step C) in 75 mL of pyridine cooled to −30° C., was added 1.93 mL (23.5 mmol) of POCl3 slowly dropwise over 5 min. The mixture was stirred 3 h, warmed to room temperature and was stirred overnite. The reaction mixture was poured into ice water, and extracted several times with EtOAc. The combined EtOAc extracts were dried (MgSO4), concentrated and chromatographed over SiO2 (eluted with 0% to 15% MeOH/EtOAc) to afford 2.57 g (51%) of 4-Methylthiazole-2-carboxylic acid (2-acetyl-5-methoxyphenyl)amide as a yellow solid: 1H NMR (500 MHz, CDCl3) δ 1.41 (d, J=6.7 Hz, 6H), 2.64 (s, 3H), 3.24 (m, 1H), 3.91 (s, 3H), 6.67 (dd, J=9, 2.5 Hz, 1H), 7.18 (s, 1H), 7.86 (d, J=9 Hz, 1H), 8.56 (d, J=2.5 Hz, 1H), 13.48 (s, 1H).

Workup

temperaturewarmed to room temperature
stirringwas stirred overnite
extractionextracted several times with EtOAc
dry with materialThe combined EtOAc extracts were dried (MgSO4)
concentrationconcentrated
customchromatographed over SiO2 (eluted with 0% to 15% MeOH/EtOAc)

Sources & evidence

ORD record: ord-8cbb0751e2fe43f897b2b89b67b23c5b
Source dataset: uspto-grants-2005_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06867185B2

Reaction notes

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