Ethanol → HCID 71625158, compound

HRID 589610Notes

Reaction equation

HRID 589610 reaction equation
Cl[C:2]1C=C(SC2C3C(=CC(C)=CC=3)NC=2CCC(N)=O)C=C(Cl)[CH:7]=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.CCO>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][CH2:2][CH3:7])=[O:44])=[CH:30][CH:31]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 65578Oxalyl chlorideHCID 71625398HCID 71625398, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625158HCID 71625158, compoundYield 76%

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 EtOH (5 mL) provided 61 mg (76%) of product 10 as a white solid, mp 158-160° C. 1H NMR (300 MHz, DMSO-d6) δ 1.24 (t, J=7 Hz, 3H), 2.34 (s, 3H), 4.30 (q, J=7 Hz, 2H), 7.05 (d, J=8 Hz, 2H), 7.16 (d, J=8 Hz, 1H), 7.26-7.29 (m, 3H), 7.46 (d, J=9 Hz, 1H), 12.38 (s, 1H). LC-MS (CI): m/z 346.1 [(M+H)+ C18H16ClNO2S requires 345.06]. Purity (100%). Calcd for C18H16ClNO2S: C, 62.51; H, 4.66; N, 4.05; S, 9.27; Cl, 10.25. Found: C, 62.37; H, 4.60; N, 3.95; S, 9.21; Cl, 10.30.

Sources & evidence

ORD record
ord-7efcd54a6f0c42558b5aa2684529dd95
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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