Ammonium Chloride → HCID 69939571, compound

HRID 1058463Notes

Reaction equation

HRID 1058463 reaction equation
[ClH:1].[CH3:2][S:3][C:4]1[S:8][C:7]([C:9]([NH2:11])=[NH:10])=[CH:6][C:5]=1[C:12]1[O:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1.CSC1SC(C(OC)=O)=CC=1C1OC=C(C2C=CC=CC=2)N=1.[Cl-].[NH4+].C[Al](C)C>C1(C)C=CC=CC=1>[ClH:1].[ClH:1].[CH3:2][S:3][C:4]1[S:8][C:7]([C:9]([NH2:11])=[NH:10])=[CH:6][C:5]=1[C:12]1[O:13][CH:14]=[C:15]([C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=2)[N:16]=1

Participants

6

Reactant 4

HCID 25517Ammonium ChlorideHCID 16682925TrimethylaluminumHCID 18536895HCID 18536895, compoundHCID 18537238HCID 18537238, compound

Product 1

HCID 69939571HCID 69939571, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent2×

Procedure

5-Methylthio-4-(4-phenyl(1,3-oxazol-2-yl))thiophene-2-carboxamidine hydrochloride: Methyl 5-methylthio-4-(4-phenyl(1,3-oxazol-2-yl))thiophene-2-carboxylate (80.3 mg, 0.242 mmol, as prepared in the previous step) was treated according to the procedure in Example 10, step (b) using 155 mg (2.90 mmol) of ammonium chloride in 1.45 mL of toluene and 1.45 mL (2.90 mmol) of 2 M trimethylaluminum in toluene. The resulting light yellow solid was chromatographed on a 5 g silica SPE column (Waters Sep-Pak) with 10% MeOH—CH2Cl2 to give a light yellow resin. Crystallization from MeOH—Et2O (ca. 1:3) afforded the title compound as a yellow solid (62.2 mg, 82%). 1H-NMR (300 MHz, DMSO-d6) δ 9.39 (broad s, 2H), 8.97 (broad s, 2H), 8.78 (s, 1H), 8.60 (s, 1H), 7.89 (d, 2H, J=7 Hz), 7.49 (t, 2H, J=7 Hz), 7.38 (t, 1H, J=7 Hz), and 2.80 (s, 3H). Mass spectrum (ESI) calcd. for C15H13N3OS2: 316.1(M+H). Found: 316.2.

Workup

  1. additionwas treated
  2. customThe resulting light yellow solid was chromatographed on a 5 g silica SPE column (Waters Sep-Pak) with 10% MeOH—CH2Cl2
  3. customto give a light yellow resin
  4. customCrystallization from MeOH—Et2O (ca. 1:3)

Sources & evidence

ORD record
ord-21b17503551d4b43a7b6acb08761d29b
Source dataset
uspto-grants-2003_02
Patent number
US06515002B2

Reaction notes

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