Triethylamine → HCID 20406198, compound

HRID 2164306Notes

Reaction equation

HRID 2164306 reaction equation
[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([CH3:8])=[CH:4][C:3]=1[C:9]([C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:10].[CH2:18]([S:21][CH2:22][C:23]([NH2:25])=[O:24])[CH2:19][CH3:20].C(OCl)(C)(C)C.C(N(CC)CC)C>C(Cl)Cl>[NH2:1][C:2]1[C:3]([C:9](=[O:10])[C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[CH:4][C:5]([CH3:8])=[CH:6][C:7]=1[CH:22]([S:21][CH2:18][CH2:19][CH3:20])[C:23]([NH2:25])=[O:24]

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 521297Tert-Butyl hypochloriteHCID 10966280Methanone, (2-amino-5-methylphenyl)(4-fluorophenyl)-HCID 21196834HCID 21196834, compound

Product 1

HCID 20406198HCID 20406198, compoundYield 86%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-70 °C

Procedure

To a mixture of 45.8 g (0.2 mole) of (2-amino-5-methylphenyl)(4-fluorophenyl)methanone and 26.6 g (0.2 mole) of 2-(1-propylthio)acetamide and 700 ml of methylene chloride cooled to -70° C. was added 23 g (0.2 mole) of 95% t-butoxychloride over a 40 minute period. The mixture was kept at -70° C. for 2 additional hours and then 21 g (0.2 mole of triethylamine was added dropwise. The mixture was allowed to warm to room temperature and was washed with water. The organic layer was concentrated and the residue was triturated with isopropyl ether to give 61.7 g (86%) of the titled compound as yellow crystals, m.p. 130.5°-132.5° C.

Workup

  1. customwas kept at -70° C. for 2 additional hours
  2. temperatureto warm to room temperature
  3. washwas washed with water
  4. concentrationThe organic layer was concentrated
  5. customthe residue was triturated with isopropyl ether

Sources & evidence

ORD record
ord-a6f3b04eff6a45fc9660fe2e28882def
Source dataset
uspto-grants-1985_03
Patent number
US04503073

Reaction notes

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