Benzyl Alcohol → HCID 71625285, compound

HRID 589612Notes

Reaction equation

HRID 589612 reaction equation
ClC1C=C(SC2[C:18]3[C:13](=[CH:14][C:15]([CH3:19])=[CH:16][CH:17]=3)NC=2CCC(N)=O)C=C(Cl)C=1.[Cl:25][C:26]1[CH:31]=[CH:30][C:29]([S:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([CH3:42])[CH:40]=3)[NH:35][C:34]=2[C:43]([OH:45])=[O:44])=[CH:28][CH:27]=1.C(Cl)(=O)C(Cl)=O.C(O)C1C=CC=CC=1.N1C=CC=CC=1>C1COCC1>[Cl:25][C:26]1[CH:27]=[CH:28][C:29]([S:32][C:33]2[C:41]3[C:36](=[CH:37][CH:38]=[C:39]([CH3:42])[CH:40]=3)[NH:35][C:34]=2[C:43]([O:45][CH2:19][C:15]2[CH:16]=[CH:17][CH:18]=[CH:13][CH:14]=2)=[O:44])=[CH:30][CH:31]=1

Participants

7

Reactant 5

HCID 244Benzyl AlcoholHCID 1049PyridineHCID 65578Oxalyl chlorideHCID 71625398HCID 71625398, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625285HCID 71625285, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the method used to prepare 24a, the use of 1b (0.23 mmol) and oxalyl chloride in THF followed by allowing the intermediate acid chloride to react with benzyl alcohol (35 μL, 0.34 mmol) in presence of pyridine (54 μL, 0.68 mmol) provided 35 mg (37%) of product 16 as a pale yellow foam. 1H NMR (300 MHz, DMSO-d6) δ 2.34 (s, 3H), 5.35 (s, 2H), 7.00 (d, J=9 Hz, 2H), 7.20 (d, J=9 Hz, 1H), 7.26 (d, J=9 Hz, 2H), 7.29-7.38 (m, 6H), 7.47 (d, J=9 Hz, 1H), 12.44 (s, 1H). LC-MS (CI): m/z 408.1 [(M+H)+ C23H18ClNO2S requires 407.6]. Purity (100%). Calcd for C23H18ClNO2S: C, 67.72; H, 4.45; N, 3.43; S, 7.86; Cl, 8.69. Found: C, 67.53; H, 4.55; N, 3.42; S, 8.09; Cl, 8.45.

Sources & evidence

ORD record
ord-edd89d17b8394ddda91ec95f09943216
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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