Thionyl Chloride → HCID 58474527, compound

HRID 1400820Notes

Reaction equation

HRID 1400820 reaction equation
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-:28])=[O:27])[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:19]=[CH:18][C:17]([CH2:20]O)=[CH:16][CH:15]=3)[S:13][C:6]=12.S(Cl)([Cl:31])=O>>[Cl:31][CH2:20][C:17]1[CH:16]=[CH:15][C:14]([C:12]2[S:13][C:6]3[C:7](=[N:8][CH:9]=[CH:10][C:5]=3[O:4][C:3]3[CH:22]=[CH:23][C:24]([N+:26]([O-:28])=[O:27])=[CH:25][C:2]=3[F:1])[CH:11]=2)=[N:19][CH:18]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 58474695HCID 58474695, compound

Product 1

HCID 58474527HCID 58474527, compoundYield 88%

Conditions

Temperature
0 °C

Procedure

A solution of 101 (2.23 g, 5.61 mmol) in thionyl chloride (8.14 mL) under nitrogen was stirred at RT overnight. The reaction mixture was cooled down to 0° C., and ice was added. The resultant suspension was stirred for 1 h, the solid was collected by filtration, rinsed with water and dried under high vacuum to afford the title compound 102 (2.06 g, 4.96 mmol, 88% yield) as a yellow fluffy solid which was used in the next step without any further purification. MS (m/z): 416.4 and 418.4 (M+H).

Workup

  1. additionice was added
  2. filtrationthe solid was collected by filtration
  3. washrinsed with water
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-7026f47a38544234a7cb141b5b2686eb
Source dataset
uspto-grants-2014_12
Patent number
US08906852B2

Reaction notes

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