2-Aminothiazole → HCID 54704472, compound

HRID 2082673Notes

Reaction equation

HRID 2082673 reaction equation
[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][S:14][C:4]=2[S:5](=[O:13])(=[O:12])[CH2:6][C:7]=1[C:8]([O:10]C)=O.[NH2:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1>C1(C)C(C)=CC=CC=1>[OH:1][C:2]1[C:3]2[CH:16]=[CH:15][S:14][C:4]=2[S:5](=[O:13])(=[O:12])[CH2:6][C:7]=1[C:8]([NH:17][C:18]1[S:19][CH:20]=[CH:21][N:22]=1)=[O:10]

Participants

4

Reactant 2

HCID 21552-AminothiazoleHCID 54704473HCID 54704473, compound

Product 1

HCID 54704472HCID 54704472, compoundYield 21.3%

Reagents, catalysts & solvents 1

HCID 7237O-XyleneSolvent

Conditions

Temperature
5 °C

Procedure

A mixture of methyl 4-hydroxy-6H-thieno[2,3-b]thiopyran-5-carboxylate 7,7-dioxide (5.2 g, 0.02 mole), 2-aminothiazole (3.0 g, 0.03 mole) and xylene (175 ml) is warmed and filtered from the polymeric products. The filtrate is refluxed for 30 min. when some more polymeric product is formed. It is filtered again, and the filtrate refluxed for 1.5 hrs. The mixture is cooled to 5° C. in an ice-bath, and the resulting crystalline product is collected. It is dissolved in THF, treated with charcoal and filtered. The filtrate is concentrated to give the desired product (1.4 g, 21%), m.p. 215°-216° C. IR (Nujol) 3100 (broad, NH and OH); 1590 (CONH); 1155 (SO2) cm-1. NMR (DMSO) δ 11.0 (b, ~2, NH and OH); 8.1 (d, 1, C3 '); 7.5 (m, 2, C2 -C3); 7.15 (d, 1, C4 '); 4.6 (s, 2, CH2). λmaxEtOH 360 (14,600), 267 (12,400), 246 (11,600) mμ; mol. ion. 328.

Workup

  1. temperatureis warmed
  2. filtrationfiltered from the polymeric products
  3. temperatureThe filtrate is refluxed for 30 min. when some more polymeric product
  4. customis formed
  5. filtrationIt is filtered again
  6. temperaturethe filtrate refluxed for 1.5 hrs
  7. customthe resulting crystalline product is collected
  8. dissolutionIt is dissolved in THF
  9. additiontreated with charcoal
  10. filtrationfiltered
  11. concentrationThe filtrate is concentrated

Sources & evidence

ORD record
ord-de13931e011f41b0959ccbc0dee19ae5
Source dataset
uspto-grants-1978_04
Patent number
US04082757

Reaction notes

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