Benzyl Alcohol → HCID 71625286, compound

HRID 589616Notes

Reaction equation

HRID 589616 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]=[CH:39][C:40]=3[CH3:42])[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]=[CH:39][C:40]=3[CH3:42])[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 71625288HCID 71625288, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625286HCID 71625286, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Following the method used to prepare 24a, the use of 1a (0.21 mmol) and oxalyl chloride in THF followed by allowing the intermediate acid chloride to react with benzyl alcohol (33 μL, 0.32 mmol) in the presence of pyridine (54 μL, 0.68 mmol) provided 17 mg (20%) of product 17 as a pale yellow foam. 1H NMR (300 MHz, DMSO-d6) δ 2.59 (s, 3H), 5.36 (s, 2H), 6.89 (d, J=7 Hz, 1H), 6.95 (d, J=9 Hz, 1H), 7.22 (d, J=8 Hz, 2H), 7.24-7.27 (m, 2H), 7.31-7.39 (m, 5H), 7.43 (d, J=8 Hz, 1H), 12.45 (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, 67.48; H, 4.43; N, 3.42; S, 7.85; Cl, 8.98.

Sources & evidence

ORD record
ord-e2144f57e7d347cf80265ffb5295f10b
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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