Oxalyl chloride → HCID 71625155, compound

HRID 589608Notes

Reaction equation

HRID 589608 reaction equation
Cl[C:2]1C=C(SC2C3C(=CC(C)=CC=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>CO>[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][CH3:2])=[O:44])=[CH:30][CH:31]=1

Participants

5

Reactant 3

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

Product 1

HCID 71625155HCID 71625155, compoundYield 90%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Following the method used to prepare 24a, the use of 1b (0.51 g, 1.60 mmol) and oxalyl chloride (0.32 mL, 3.65 mmol) followed by allowing the intermediate acid chloride to react with MeOH (5 mL) provided 0.95 g (90%) of product 7 as a white solid, mp 230-233° C. 1H NMR (300 MHz, DMSO-d6) δ 2.34 (s, 3H), 3.84 (s, 3H), 7.05 (d, J=8 Hz, 2H), 7.16-7.20 (m, 1H), 7.25-7.28 (m, 3H), 7.45 (d, J=8 Hz, 1H), 12.41 (s, 1H). LC-MS (CI): m/z 332.1 [(M+H)+ C17H14ClNO2S requires 331.04]. Purity (100%). Calcd for C17H14ClNO2S.0.2H2O: C, 60.87; H, 4.33; N, 4.18; S, 9.56; Cl, 10.57. Found: C, 60.89; H, 4.08; N, 4.14; S, 9.81; Cl, 10.77.

Sources & evidence

ORD record
ord-338515a142024082907b201ad856ad9f
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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