Water → HCID 131712419, compound

HRID 1578154Notes

Reaction equation

HRID 1578154 reaction equation
C(N(CC)CC)C.[C:8]([C:12]1[CH:17]=[C:16]([N:18]=[O:19])[CH:15]=[C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]=1[OH:24])([CH3:11])([CH3:10])[CH3:9].[CH3:25][S:26][C:27](=[N:29][O:30][C:31]([N:33]([S:35][N:36]([C:38](F)=[O:39])[CH3:37])[CH3:34])=[O:32])[CH3:28].O>CCOCC.CCCCCC>[CH3:25][S:26][C:27](=[N:29][O:30][C:31]([N:33]([S:35][N:36]([C:38]([O:19][N:18]=[C:16]1[CH:17]=[C:12]([C:8]([CH3:11])([CH3:10])[CH3:9])[C:13](=[O:24])[C:14]([C:20]([CH3:23])([CH3:22])[CH3:21])=[CH:15]1)=[O:39])[CH3:37])[CH3:34])=[O:32])[CH3:28]

Participants

7

Reactant 4

HCID 962WaterHCID 8471TriethylamineHCID 70383Phenol, 2,6-bis(1,1-dimethylethyl)-4-nitroso-HCID 54165239HCID 54165239, compound

Product 1

HCID 131712419HCID 131712419, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolvent2×HCID 8058HexaneSolvent

Procedure

A solution of 1.2 g of triethylamine in 10 ml of dry ether was added dropwise to a mixture of 2.4 g of 2,6-di-t-butyl-4-nitrosophenol and 2.7 g of N-[[[N-[[N-fluorocarbonyl-N-methylaminothio]]-N-methylaminocarbonyloxy]]]ethanimidothioic acid methyl ester suspended in 40 ml of dry ether at a temperature below 25°. The mixture was stirred at room temperature for 50 minutes. Then, water and hexane were added to the mixture. The product was collected by filtration, washed with water, hexane, and air-dried to give 4.1 g of N-[[[N-[[3,5-bis-(1,1-dimethylethyl)-4-oxo-2,5-cyclohexadien-1-yli-deneaminooxycarbonyl]-N-methylaminothio]]-N-methylaminocarbonyloxy]]ethanimidothioic acid methyl ester, m.p. 160°-161.6°.

Workup

  1. filtrationThe product was collected by filtration
  2. washwashed with water, hexane
  3. customair-dried

Sources & evidence

ORD record
ord-1adcc4380ca242b894b03c38bce7cc91
Source dataset
uspto-grants-1981_09
Patent number
US04291054

Reaction notes

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