Ammonia → HCID 86649901, compound

HRID 1803134Notes

Reaction equation

HRID 1803134 reaction equation
[NH3:1].[N:2]([C:5]1[CH:10]=[CH:9][C:8]([C:11]2[O:15][N:14]=[C:13]([CH3:16])[CH:12]=2)=[C:7]([O:17][CH3:18])[CH:6]=1)=[C:3]=[S:4]>CO>[CH3:18][O:17][C:7]1[CH:6]=[C:5]([NH:2][C:3]([NH2:1])=[S:4])[CH:10]=[CH:9][C:8]=1[C:11]1[O:15][N:14]=[C:13]([CH3:16])[CH:12]=1

Participants

4

Reactant 2

HCID 222AmmoniaHCID 86649900HCID 86649900, compound

Product 1

HCID 86649901HCID 86649901, compoundYield 99.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Step H (4): Methanolic ammonia (1.3 mL, 9.28 mmol) was added to a flask charged with 5-(4-isothiocyanato-2-methoxyphenyl)-3-methylisoxazole (508 mg, 2.063 mmol) in MeOH (4.6 mL). After stirring at rt for 24 h, the reaction mixture was concentrated to dryness in vacuo to afford 1-(3-methoxy-4-(3-methylisoxazol-5-yl)phenyl)thiourea (540 mg, 2.051 mmol, 99% yield). LC-MS (M+H)+ 264.2. 1H NMR (400 MHz, methanol-d4) δ ppm 7.82 (d, J=8.56 Hz, 1 H) 7.49-7.54 (m, 1 H) 6.99 (dd, J=8.56, 2.01 Hz, 1 H) 6.67 (s, 1 H) 3.96 (s, 3 H) 2.30 (s, 3 H).

Workup

  1. concentrationthe reaction mixture was concentrated to dryness in vacuo

Sources & evidence

ORD record
ord-dc0ba05f50c440229a3a7891f1548b48
Source dataset
uspto-grants-2013_01
Patent number
US08349880B2

Reaction notes

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