Hydrochloric Acid → 2-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)benzene-propanamide

HRID 648739Notes

Reaction equation

HRID 648739 reaction equation
C([Li])CCC.[S:6]1[CH:10]=[CH:9][N:8]=[C:7]1[NH:11][C:12](=[O:14])[CH3:13].[Cl:15][CH:16]([C:18]1[O:23][C:22](=[O:24])[C:21]2[CH:25]=[CH:26][CH:27]=[CH:28][C:20]=2[N:19]=1)[CH3:17].Cl>O1CCCC1.O.CCCCCC>[Cl:15][CH:16]([CH3:17])[C:18]([NH:19][C:20]1[CH:28]=[CH:27][CH:26]=[CH:25][C:21]=1[C:22](=[O:24])[CH2:13][C:12]([NH:11][C:7]1[S:6][CH:10]=[CH:9][N:8]=1)=[O:14])=[O:23]

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 176252-AcetamidothiazoleHCID 134230792-(1-Chloroethyl)-4H-3,1-benzoxazin-4-oneHCID 178418339Butyllithium

Product 1

HCID 134230852-[(2-chloro-1-oxo-propyl)-amino]-beta-oxo-N-(2-thiazolyl)benzene-propanamideYield 70.5%

Reagents, catalysts & solvents 3

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent2×HCID 8058HexaneSolvent

Procedure

191 ml of a solution of 1.4M of n-butyllithium per liter of hexane were added under argon at 0° C. to a solution of 19.05 g of N-(2-thiazolyl)-acetamide in 580 ml of tetrahydrofuran and then a solution of 14.04 g of the product of Step A in 100 ml of tetrahydrofuran were added thereto at -70° to -75° C. The mixture was poured into a mixture of water and 2N hydrochloric acid and the mixture was vacuum filtered. The product was washed with water and dried under reduced pressure to obtain 16.6 g of 2-[(2-chloro-1-oxo-propyl)-amino]-β-oxo-N-(2-thiazolyl)-benzene-propanamide melting at 204° C.

Workup

  1. customat -70° to -75° C
  2. filtrationfiltered
  3. washThe product was washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-8c97190bbced4c1682e62062dbca5595
Source dataset
uspto-grants-1988_04
Patent number
US04736033

Reaction notes

Loading…