Chloroacetyl chloride → HCID 54084673, compound

HRID 1389948Notes

Reaction equation

HRID 1389948 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH:9]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=2[Cl:23])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1.[Cl:24][CH2:25][C:26](Cl)=[O:27]>CC1C=CC=CC=1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([N:8]([C:26](=[O:27])[CH2:25][Cl:24])[CH:9]([C:15]2[C:20]([Cl:21])=[CH:19][CH:18]=[C:17]([Cl:22])[C:16]=2[Cl:23])[C:10]([O:12][CH2:13][CH3:14])=[O:11])=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 6577Chloroacetyl chlorideHCID 20295995HCID 20295995, compound

Product 1

HCID 54084673HCID 54084673, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
80 °C

Procedure

A mixture of 3 parts of ethyl α-[(4-bromophenyl)amino]-2,3,6-trichlorobenzeneacetate and 4.5 parts of 2-chloroacetyl chloride is stirred for 4 hours at 80° C. The mixture is taken up twice in methylbenzene and the latter is evaporated each time. The oily residue solidifies on triturating in petroleumether. The latter is decanted and the residue is crystallized from 2,2'-oxybispropane. The product is filtered off and dried, yielding a first fraction of 1.7 parts of ethyl α-[(4-bromophenyl) (2-chloroacetyl)-amino]-2,3,6-trichlorobenzeneacetate; mp. 140.8° C. The mother liquor is concentrated and a second fraction of 1.2 parts of ethyl α-[(4-bromophenyl) (2-chloroacetyl)amino]-2,3,6-trichlorobenzeneacetate is filtered off.

Workup

  1. customthe latter is evaporated each time
  2. customon triturating in petroleumether
  3. customThe latter is decanted
  4. customthe residue is crystallized from 2,2'-oxybispropane
  5. filtrationThe product is filtered off
  6. customdried

Sources & evidence

ORD record
ord-4b3e795b4c624053b3e458cf977605b4
Source dataset
uspto-grants-1981_01
Patent number
US04246429

Reaction notes

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