Thionyl Chloride → HCID 86626008, compound

HRID 1712913Notes

Reaction equation

HRID 1712913 reaction equation
S(Cl)(Cl)=O.[CH:5]1[N:6]=[CH:7][N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[CH:22]=[CH:21][C:17]([C:18]([OH:20])=O)=[CH:16][CH:15]=3)[C:9]=12.Cl.[CH3:24][NH:25][O:26][CH3:27].C(N(C(C)C)CC)(C)C>C(Cl)(Cl)Cl>[CH:5]1[N:6]=[CH:7][N:8]2[CH2:13][CH2:12][O:11][CH:10]([C:14]3[CH:15]=[CH:16][C:17]([C:18]([N:25]([O:26][CH3:27])[CH3:24])=[O:20])=[CH:21][CH:22]=3)[C:9]=12

Participants

6

Reactant 4

HCID 24386Thionyl ChlorideHCID 81138Methanamine, N-methoxy-, hydrochloride (1:1)HCID 81531DiisopropylethylamineHCID 68440102HCID 68440102, compound

Product 1

HCID 86626008HCID 86626008, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
2.5 °C

Procedure

9.30 mmol of thionyl chloride are added to a solution of 3.10 mmol of 4-(5,6-dihydro-8H-imidazo[5,1-c][1,4]oxazin-8-yl)benzoic acid in 5 ml of chloroform. The reaction mixture is heated to reflux for 3 hours and then evaporated. The residue is stripped with toluene and then taken up in 10 ml of dichloromethane. The reaction solution is cooled to 0-5° C., and 3.10 mmol of N,O-dimethylhydroxylamine hydrochloride, followed by 15.5 mmol of diisopropylethylamine, are added. The reaction mixture is stirred at room temperature for 16 hours and filtered through Hyflo, and the filtrate is evaporated. The title compound is obtained as a yellowish oil from the residue by flash chromatography (SiO2 60F). Rf=0.13 (dichloromethane-2M ammonia in ethanol 97:3); Rt=4.00.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 3 hours
  3. customevaporated
  4. additionare added
  5. filtrationfiltered through Hyflo
  6. customthe filtrate is evaporated

Sources & evidence

ORD record
ord-273f69f4d40840a491e3c68422e30d60
Source dataset
uspto-grants-2010_09
Patent number
US07795253B2

Reaction notes

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