Hydrochloric Acid → Ethyl 2-[(2,2-dichloro-1-oxoethyl)-amino]-beta-oxo-alpha-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoate

HRID 1789217Notes

Reaction equation

HRID 1789217 reaction equation
[Cl:1][CH:2]([Cl:18])[C:3]1[O:8][C:7](=[O:9])[C:6]2[CH:10]=[CH:11][CH:12]=[C:13]([C:14]([F:17])([F:16])[F:15])[C:5]=2[N:4]=1.[S:19]1[CH:23]=[CH:22][N:21]=[C:20]1[NH:24][C:25](=[O:32])[CH2:26][C:27]([O:29][CH2:30][CH3:31])=[O:28].[OH-].[Na+].Cl>O.O1CCCC1>[Cl:1][CH:2]([Cl:18])[C:3]([NH:4][C:5]1[C:13]([C:14]([F:17])([F:16])[F:15])=[CH:12][CH:11]=[CH:10][C:6]=1[C:7](=[O:9])[CH:26]([C:25]([NH:24][C:20]1[S:19][CH:23]=[CH:22][N:21]=1)=[O:32])[C:27]([O:29][CH2:30][CH3:31])=[O:28])=[O:8]

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 14798Sodium HydroxideHCID 7339584Ethyl 3-oxo-3-(1,3-thiazol-2-ylamino)propanoateHCID 133813212-(Dichloromethyl)-8-(trifluoromethyl)-4H-3,1-benzoxazin-4-one

Product 1

HCID 20188954Ethyl 2-[(2,2-dichloro-1-oxoethyl)-amino]-beta-oxo-alpha-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoateYield 98.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
20 °C

Procedure

At 20° C., 150 g of 2-dichloromethyl-8-trifluoromethyl-4H-3,1-benzoxazine-4-one, 120 g of ethyl 3-(2-thiazolylamino)-3-oxo-propanoate and 1.5 liters of tetrahydrofuran were mixed together and stirred for 30 minutes and then, while maintaining the temperature at 20° C., 40 g of sodium hydroxide in flakes were added thereto. After stirring the mixture at 20° C. for two hours, it was poured into a mixture of 4.5 liters of water and 150 ml of concentrated hydrochloric acid and the mixture was stirred at 0° to +5° C. for 30 minutes. The crystals formed were separated, rinsed with water and dried to obtain 255 g of ethyl 2-[(2,2-dichloro-1-oxoethyl)-amino]-β-oxo-α-[(2-thiazolylamino)-carbonyl]-3-(trifluoromethyl)-benzene-propanoate melting at 90° C.

Workup

  1. stirringAfter stirring the mixture at 20° C. for two hours
  2. stirringthe mixture was stirred at 0° to +5° C. for 30 minutes
  3. customThe crystals formed
  4. customwere separated
  5. washrinsed with water
  6. customdried

Sources & evidence

ORD record
ord-6c40390b38bd4fa3b03a4392347326e9
Source dataset
uspto-grants-1987_08
Patent number
US04687857

Reaction notes

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