Hydrochloric Acid → HCID 13394285, compound

HRID 2164302Notes

Reaction equation

HRID 2164302 reaction equation
[NH2:1][C:2]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][C:9]([F:12])=[CH:8][CH:7]=1)=[O:5].CC[C:20](OCC)=[S:21].[C:25]([O:29]Cl)(C)(C)[CH3:26].C(N(CC)CC)C.Cl>C(Cl)Cl>[F:17][C:14]1[CH:15]=[C:16]2[C:2](=[C:3]([C:4](=[O:5])[C:6]3[CH:7]=[CH:8][C:9]([F:12])=[CH:10][CH:11]=3)[CH:13]=1)[NH:1][C:25](=[O:29])[CH:26]2[S:21][CH3:20]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 12284386Ethyl methylthioacetateHCID 13408103HCID 13408103, compound

Product 1

HCID 13394285HCID 13394285, compoundYield 45.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

A solution of 46.6 g (0.2 mole) of 2-amino-4',5-difluorobenzophenone in 1300 ml of methylene chloride was cooled to -65° C. and 26.8 g (0.2 mole) of ethyl methylthioacetate was added. The cold mixture was stirred vigorously while 23.0 g (0.2 mole) of 95% tertiary butoxy chloride was added dropwise. The mixture was stirred at -70° C. for one hour, then 23 g (0.22 mole) of triethylamine was added. The mixture was allowed to warm to room temperature and 10 ml of concentrated hydrochloric acid was added. The mixture was heated at reflux with vigorous stirring for 2 hrs. The organic phase was separated and the residue was crystallized from ethyl acetate to give 28.9 g (45%) of the titled compound as off-white crystals, m.p. 171.0°-172.5° C.

Workup

  1. additionwas added dropwise
  2. temperatureto warm to room temperature
  3. temperatureThe mixture was heated
  4. temperatureat reflux
  5. stirringwith vigorous stirring for 2 hrs
  6. customThe organic phase was separated
  7. customthe residue was crystallized from ethyl acetate

Sources & evidence

ORD record
ord-b333af6489a14fb982b6006eb2da663b
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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