Ammonia → HCID 71625873, compound

HRID 589607Notes

Reaction equation

HRID 589607 reaction equation
ClC1C=C(SC2C3C(=CC(C)=CC=3)[NH:12]C=2CCC(N)=O)C=C(Cl)C=1.[Cl:25][C:26]1[CH:27]=[C:28]([S:33][C:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[NH:36][C:35]=2[CH2:44][C:45]([OH:47])=O)[CH:29]=[C:30]([Cl:32])[CH:31]=1.C(Cl)(=O)C(Cl)=O.N>O1CCOCC1>[Cl:25][C:26]1[CH:27]=[C:28]([S:33][C:34]2[C:42]3[C:37](=[CH:38][C:39]([CH3:43])=[CH:40][CH:41]=3)[NH:36][C:35]=2[CH2:44][C:45]([NH2:12])=[O:47])[CH:29]=[C:30]([Cl:32])[CH:31]=1

Participants

6

Reactant 4

HCID 222AmmoniaHCID 65578Oxalyl chlorideHCID 71625747HCID 71625747, compoundHCID 71625872HCID 71625872, compound

Product 1

HCID 71625873HCID 71625873, compoundYield 80%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

Following the method used to prepare 24a, the use of 53 (0.35 g, 0.96 mmol) and oxalyl chloride (120 μL, 1.44 mmol) followed by allowing the intermediate acid chloride to react with ammonia in dioxane provided 0.28 g (80%) of product 24b as an off white solid, mp 197° C. 1H NMR (300 MHz, DMSO-d6) δ 2.40 (s, 3H), 3.70 (s, 2H), 6.90 (d, J=8 Hz, 1H), 6.99-7.01 (m, 2H), 7.08 (brs, 1H), 7.20 (d, J=8 Hz, 1H), 7.25-7.28 (m, 2H), 7.54 (brs, 1H), 11.65 (brs, 1H). LC-MS (CI): m/z 365.0, 367.0 [(M+H)+ C17H14Cl2NO2S requires 364.0]. Purity (100%). Calcd for C17H14Cl2NO2S: C, 55.90; H, 3.86; N, 7.67; S, 8.78; Cl, 19.41. Found: C, 55.61; H, 3.90; N, 7.68; S, 8.59; Cl, 19.67.

Sources & evidence

ORD record
ord-e234154716494b2b84c40faa3b6ebada
Source dataset
uspto-grants-2016_01
Patent number
US09233921B2

Reaction notes

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