Ammonia → HCID 20213850, compound

HRID 1906061Notes

Reaction equation

HRID 1906061 reaction equation
[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:20])([F:19])[F:18])=[CH:13][C:12]=2[Cl:21])=[CH:6][C:5]=1[NH:22][CH2:23][CH2:24][C:25](O)=[O:26])([O-:3])=[O:2].C(Cl)Cl.ClC(OC)=O.[NH3:36]>C(N(CC)CC)C>[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([O:10][C:11]2[CH:16]=[CH:15][C:14]([C:17]([F:18])([F:19])[F:20])=[CH:13][C:12]=2[Cl:21])=[CH:6][C:5]=1[NH:22][CH2:23][CH2:24][C:25]([NH2:36])=[O:26])([O-:3])=[O:2]

Participants

6

Reactant 4

HCID 222AmmoniaHCID 6344DichloromethaneHCID 6586Methyl chloroformateHCID 19858595HCID 19858595, compound2×

Product 1

HCID 20213850HCID 20213850, compound

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

88 g of N-[2-nitro-5-(2-chloro-4-trifluoromethylphenoxy)phenyl]-3-aminopropionic acid (compound 3) are added to 500 ml of methylene chloride with 34.3 ml of triethylamine at -25° C. With stirring, 22.8 ml of methyl chloroformate are run in over 30 minutes and stirring is continued at -10° to -20° C. After 2 hours, 40 ml of ammonia solution are added and the reaction mixture is warmed to room temperature. The mixture is then washed with water and the organic phase is concentrated. The residue is recrystallised from ethyl acetate/hexane. The product has a melting point of 137°-138° C.

Workup

  1. customare run in over 30 minutes
  2. stirringstirring
  3. customis continued at -10° to -20° C
  4. washThe mixture is then washed with water
  5. concentrationthe organic phase is concentrated
  6. customThe residue is recrystallised from ethyl acetate/hexane

Sources & evidence

ORD record
ord-ed816b24a79b463cb621cf23ae878093
Source dataset
uspto-grants-1987_03
Patent number
US04649212

Reaction notes

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