Triethylamine → HCID 20552969, compound

HRID 1446825Notes

Reaction equation

HRID 1446825 reaction equation
[NH2:1][C:2]1[CH:15]=[CH:14][C:13]([Cl:16])=[CH:12][C:3]=1[C:4]([C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][CH:7]=1)=[O:5].C(OCl)(C)(C)C.[CH3:23][S:24][CH2:25][C:26]([NH:28][CH3:29])=[O:27].C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:4](=[O:5])[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][CH:11]=2)=[CH:12][C:13]([Cl:16])=[CH:14][C:15]=1[CH:25]([S:24][CH3:23])[C:26]([NH:28][CH3:29])=[O:27]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 128702-Amino-5-chlorobenzophenoneHCID 521297Tert-Butyl hypochloriteHCID 13553138HCID 13553138, compound

Product 1

HCID 20552969HCID 20552969, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 38.3 g (0.166 mole) of 2-amino-5-chlorobenzophenone in 1 liter of methylene chloride cooled to -70° C. under an atmosphere of nitrogen was added 18.05 g (0.167 mole) of t-butylhypochlorite. The solution was stirred for 15 min and then a solution of 20.3 g (0.171 mole) of 2-methylthio-N-methylacetamide in 100 ml of methylene chloride was added. The solution was stirred at -70° C. for 2 hrs and 25 ml of triethylamine was added. While stirring, the solution was allowed to warm to room temperature followed by extraction with water and drying of the organic layer with magnesium sulfate. The volume of the solution was reduced to about 400 ml, ether was added and the solution placed in a refrigerator at about 0° C. overnight. The solid which crystallized was dried under high vacuum for about 4 hr at 50° C. Weight of the product was 31.56 g (54.6%) which melted at 170°-171° C.

Workup

  1. stirringThe solution was stirred at -70° C. for 2 hrs
  2. stirringWhile stirring
  3. extractionfollowed by extraction with water
  4. dry with materialdrying of the organic layer with magnesium sulfate
  5. additionwas added
  6. waitthe solution placed in a refrigerator at about 0° C. overnight
  7. customThe solid which crystallized
  8. customwas dried under high vacuum for about 4 hr at 50° C

Sources & evidence

ORD record
ord-f997dfa5412f40938ecb480c82e68ee2
Source dataset
uspto-grants-1982_02
Patent number
US04313949

Reaction notes

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