Dimethylformamide → 2-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride

HRID 902774Notes

Reaction equation

[C:1](Cl)(=O)[C:2]([Cl:4])=[O:3].ClCC1[N:10]=[C:11]([C:14]2C=CC(C(O)=O)=CC=2)[S:12][CH:13]=1.CN(C=O)C.C(Cl)[Cl:29]>>[Cl:29][CH2:14][C:11]1[S:12][CH:13]=[C:1]([C:2]([Cl:4])=[O:3])[N:10]=1

Participants

Reactant 4

HCID 6228Dimethylformamide

HCID 6344Dichloromethane

HCID 65578Oxalyl chloride

HCID 167773054-[4-(Chloromethyl)-1,3-thiazol-2-yl]benzoic acid

Product 1

HCID 597024562-(Chloromethyl)-1,3-thiazole-4-carbonyl chloride

Procedure

Oxalyl chloride (3.2 mL, 36.6 mmol, 5 eq.) was added dropwise to a suspension of 4-[4-(chloromethyl)-1,3-thiazol-2-yl]benzoic acid (1.30 g, 7.32 mmol, 1 eq.) in DCM (10 mL) followed by a catalytic amount of DMF at RT. The reaction mixture was allowed to stir at RT overnight and then evaporated to give the title compound as the crude product.

Workup

customevaporated

Sources & evidence

ORD record: ord-2215436c77e94d4595b16aee59f0cd2e
Source dataset: uspto-grants-2008_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07365225B2

Reaction notes

Loading…