Pyridine → Ethyl 2-methanesulfonamidothiazol-4-ylacetate

HRID 325371

Reaction equation

HRID 325371 reaction equation
[NH2:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1.[S:13](Cl)([CH3:16])(=[O:15])=[O:14].N1C=CC=CC=1>C(Cl)Cl>[S:13]([NH:1][C:2]1[S:3][CH:4]=[C:5]([CH2:7][C:8]([O:10][CH2:11][CH3:12])=[O:9])[N:6]=1)([CH3:16])(=[O:15])=[O:14]

Participants

6

Reactant 4

HCID 1049PyridineHCID 31297Methanesulfonyl chlorideHCID 1044544-Thiazoleacetic acid, 2-amino-, ethyl esterHCID 178470764HCID 178470764, compound

Product 1

HCID 3145078Ethyl 2-methanesulfonamidothiazol-4-ylacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A mixture of ethyl 2-(2-amino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-imino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (5.6 g.), mesyl chloride (6.9 g.), pyridine (15 ml.) and methylene chloride (45 ml.) was refluxed for 5 hours. After the reaction, the reaction mixture was concentrated. The residue was poured into ice-water (150 ml.) and stirred. The precipitates were collected by filtration, washed with water and diethyl ether and dried to give pale brown powder of ethyl 2-(2-mesylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-mesylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (6.3 g.).

Workup

  1. temperaturewas refluxed for 5 hours
  2. customAfter the reaction
  3. concentrationthe reaction mixture was concentrated
  4. additionThe residue was poured into ice-water (150 ml.)
  5. filtrationThe precipitates were collected by filtration
  6. washwashed with water and diethyl ether
  7. customdried

Sources & evidence

ORD record
ord-e949e6e8af8845e688c187690f9943fd
Source dataset
uspto-grants-1984_04
Patent number
US04440766

Linked notes

Loading…