Isopropyl chloroformate → n-[2-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

HRID 898594Notes

Reaction equation

HRID 898594 reaction equation
C(OC(Cl)=O)(C)C.[Cl:8][C:9]1[CH:19]=[C:18]([C:20]([F:23])([F:22])[F:21])[CH:17]=[CH:16][C:10]=1[O:11][CH2:12][C:13]([OH:15])=O.CN1CCOCC1.[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:35]=[CH:34][C:33]=1[NH2:46]>C1COCC1>[Cl:31][C:32]1[CH:37]=[C:36]([O:38][CH2:39][CH2:40][N:41]([CH2:44][CH3:45])[CH2:42][CH3:43])[CH:35]=[CH:34][C:33]=1[NH:46][C:13](=[O:15])[CH2:12][O:11][C:10]1[CH:16]=[CH:17][C:18]([C:20]([F:23])([F:22])[F:21])=[CH:19][C:9]=1[Cl:8]

Participants

6

Reactant 4

HCID 7917Isopropyl chloroformateHCID 79724-MethylmorpholineHCID 57082476[2-(3-Chloro-4-aminophenoxy)ethyl]diethylamineHCID 59691547(2-Chloro-4-trifluoromethyl-phenoxy)-acetic acid

Product 1

HCID 59691711n-[2-Chloro-4-(2-diethylamino-ethoxy)-phenyl]-2-(2-chloro-4-trifluoromethyl-phenoxy)-acetamide

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.141 mL (1.080 mmol) chloroformic acid-isopropylester was added dropwise at −10° C. to a solution of 0.254 g (0.982 mmol) (2-chloro-4-trifluoromethyl-phenoxy)-acetic acid (Z2b) and 0.119 mL (1.080 mmol) N-methylmorpholine in 20 mL abs. THF and the mixture was stirred for a further 10 min. 0.250 g (1.031 mmol) 2-chloro-4-(2-diethylamino-ethoxy)-phenylamine (Z27b) was added, the mixture was stirred for 1 h at RT and then evaporated down i. vac. Water was added and the aqueous phase was exhaustively extracted with dichloromethane. The combined org. phases were dried over sodium sulphate, evaporated down i. vac. and the residue stirred with ether. The precipitate was filtered off, washed with ether and dried in a HV.

Workup

  1. customevaporated down i
  2. additionWater was added
  3. extractionthe aqueous phase was exhaustively extracted with dichloromethane
  4. dry with materialphases were dried over sodium sulphate
  5. customevaporated down i
  6. stirringand the residue stirred with ether
  7. filtrationThe precipitate was filtered off
  8. washwashed with ether
  9. customdried in a HV

Sources & evidence

ORD record
ord-6c174088f3e5438fb5ba7ad4fd7a9c89
Source dataset
uspto-grants-2008_04
Patent number
US07351719B2

Reaction notes

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