Thionyl Chloride → 3-(1-Benzothiophen-5-ylmethoxy)-2,6-difluorobenzenecarboxamide

HRID 415609Notes

Reaction equation

HRID 415609 reaction equation
[F:1][C:2]1[C:7]([OH:8])=[CH:6][CH:5]=[C:4]([F:9])[C:3]=1[C:10]([NH2:12])=[O:11].Cl[CH2:14][C:15]1[CH:16]=[CH:17][C:18]2[S:22][CH:21]=[CH:20][C:19]=2[CH:23]=1.S1C2C=CC(CO)=CC=2C=C1.S(Cl)(Cl)=O>>[S:22]1[C:18]2[CH:17]=[CH:16][C:15]([CH2:14][O:8][C:7]3[C:2]([F:1])=[C:3]([C:10]([NH2:12])=[O:11])[C:4]([F:9])=[CH:5][CH:6]=3)=[CH:23][C:19]=2[CH:20]=[CH:21]1

Participants

5

Reactant 4

HCID 24386Thionyl ChlorideHCID 27954461-Benzothiophen-5-ylmethanolHCID 232617225-(Chloromethyl)benzo[b]thiopheneHCID 451201362,6-Difluoro-3-hydroxybenzamide

Product 1

HCID 594030103-(1-Benzothiophen-5-ylmethoxy)-2,6-difluorobenzenecarboxamideYield 10%

Procedure

Synthesised from 2,6-difluoro-3-hydroxybenzenecarboxamide according to Method B, scheme 2. The required building block, 5-(chloromethyl)-1-benzothiophene, was synthesised by chlorination of commercially available 1-benzothiophen-5-ylmethanol with thionyl chloride. Yield 10%, mp 146-148° C., HPLC-MS (method 1): m/z 320 [M+H]+, Rt=3.95 min.

Sources & evidence

ORD record
ord-6ce73ba1af514328a8c66906ff448974
Source dataset
uspto-grants-2012_01
Patent number
US08088791B2

Reaction notes

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