Oxalyl chloride → HCID 56963456, compound

HRID 1526813Notes

Reaction equation

HRID 1526813 reaction equation
C(Cl)(=O)C(Cl)=O.[CH3:7][C:8]1[O:12][C:11]([C:13]2[CH:21]=[CH:20][C:16]([C:17](O)=[O:18])=[CH:15][CH:14]=2)=[N:10][C:9]=1[CH2:22][S:23]([C:26]1[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=1)(=[O:25])=[O:24].[CH3:33][N:34]1[C:38]([CH2:39][NH2:40])=[CH:37][N:36]=[CH:35]1>>[CH3:33][N:34]1[C:38]([CH2:39][NH:40][C:17](=[O:18])[C:16]2[CH:20]=[CH:21][C:13]([C:11]3[O:12][C:8]([CH3:7])=[C:9]([CH2:22][S:23]([C:26]4[CH:31]=[CH:30][C:29]([CH3:32])=[CH:28][CH:27]=4)(=[O:24])=[O:25])[N:10]=3)=[CH:14][CH:15]=2)=[CH:37][N:36]=[CH:35]1

Participants

4

Reactant 3

HCID 65578Oxalyl chlorideHCID 27954241-Methyl-5-aminomethylimidazoleHCID 532133574-(5-Methyl-4-{[(4-methylphenyl)sulfonyl]methyl}-1,3-oxazol-2-yl)benzoic Acid

Product 1

HCID 56963456HCID 56963456, compoundYield 82.3%

Procedure

Reaction of oxalyl chloride (111 λL, 1.27 mmol) and benzoic acid 4 (318 mg, 0.85 mmol) with subsequent coupling to (1-methyl-1H-imidazol-5-yl)methylamine (104 mg, 0.94 mmol) gave benzamide 15 (325 mg, 82%) as a white powder: mp (EtOAc) 240-242° C.; 1H NMR δ 8.93 (t, J=5.3Hz, 1 H, CONH), 7.97 (br d, J=8.5Hz, 2 H, H-2, H-6), 7.87 (br d, J=8.5Hz, 2 H, H-3, H-5), 7.67 (br d, J=8.3 Hz, 2 H, H-2′, H-6′), 7.54 (s, 1 H, H-2″), 7.42 (br d, J=8.3Hz, 2 H, H-3′, H-5′), 6.84 (s, 1 H, H-4″), 4.62 (s, 2 H, CH2SO2), 4.48 (d, J=5.3Hz, 2 H, CH2N), 3.62 (s, 3 H, NCH3), 2.40 (s, 3 H, CH3), 2.13 (s, 3 H, CH3); 13C NMR δ 165.1, 157.9, 149.8, 144.4, 138.1, 135.5, 135.4, 129.5 (2), 128.7, 128.6, 128.1 (2), 128.0 (2), 127.7, 125.9, 125.2 (2), 52.8, 32.5, 30.9, 20.9, 9.5; MS m/z 465.5 (MH+, 100%). Anal. calcd for C24H24N4O4S: C, 62.05; H, 5.21; N, 12.06. Found: C, 62.42; H, 5.24; N, 12.12%.

Sources & evidence

ORD record
ord-8dcd87151bad4dd98854e7168d45dd32
Source dataset
uspto-grants-2015_07
Patent number
US09085570B2

Reaction notes

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