Water → HCID 20254373, compound

HRID 638427Notes

Reaction equation

HRID 638427 reaction equation
[CH3:1][NH:2][C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1.Cl[C:15]([O:17][C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])=[O:16].O>N1C=CC=CC=1.C(Cl)Cl>[CH3:1][N:2]([C:3]1[S:4][CH:5]=[C:6]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[N:7]=1)[C:15]([O:17][C:18]([CH2:21][CH3:22])([CH3:20])[CH3:19])=[O:16]

Participants

6

Reactant 3

HCID 962WaterHCID 15051328Carbonochloridic acid, 1,1-dimethylpropyl esterHCID 20254369Ethyl 2-[2-(methylamino)-1,3-thiazol-4-yl]acetate

Product 1

HCID 20254373HCID 20254373, compound

Reagents, catalysts & solvents 2

HCID 1049PyridineSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of ethyl 2-(2-methylamino-1,3-thiazol-4-yl)acetate, which can be represented as ethyl 2-(2-methylimino-2,3-dihydro-1,3-thiazol-4-yl)acetate, (8 g.) in a mixture of pyridine (80 ml.) and methylene chloride (40 ml.) was dropwise added tert-pentyl chloroformate over 2 hours at -25° to -20° C. with stirring, and the mixture was stirred for 30 minutes at the same temperature. After the reaction, the reaction mixture was poured into water (200 ml.), the mixture was extracted with ethyl acetate (300 ml.), and then the organic layer was separated. The organic layer was washed with 2N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water in turn. The organic layer was dried over magnesium sulfate and then concentrated to give oil of ethyl 2-[2-(N-methyl-N-tert-pentyloxycarbonylamino)1,3-thiazol-4-yl]acetate (14.5 g.).

Workup

  1. customover 2 hours
  2. customat -25° to -20° C.
  3. stirringthe mixture was stirred for 30 minutes at the same temperature
  4. customAfter the reaction
  5. extractionthe mixture was extracted with ethyl acetate (300 ml.)
  6. customthe organic layer was separated
  7. washThe organic layer was washed with 2N hydrochloric acid, water, 5% sodium bicarbonate aqueous solution and water in turn
  8. dry with materialThe organic layer was dried over magnesium sulfate
  9. concentrationconcentrated

Sources & evidence

ORD record
ord-dcbc36494af34e8cb739755cd0f34fe8
Source dataset
uspto-grants-1985_12
Patent number
US04560765

Reaction notes

Loading…