N,N-Bis(trimethylsilyl)trifluoroacetamide → HCID 20242398, compound

HRID 483107Notes

Reaction equation

HRID 483107 reaction equation
[C:1]1([CH:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[O:8][C:9]([CH:11]2[S:16][CH2:15][CH2:14][NH:13][C:12]2=[O:17])=[O:10])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C[Si]([N:28]([Si](C)(C)C)[C:29](=[O:34])C(F)(F)F)(C)C.ClC(Cl)(Cl)C(N=C=O)=O>ClCCl>[C:18]1([CH:7]([C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)[O:8][C:9]([CH:11]2[S:16][CH2:15][CH2:14][N:13]([C:29](=[O:34])[NH2:28])[C:12]2=[O:17])=[O:10])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1

Participants

5

Reactant 3

HCID 65279N,N-Bis(trimethylsilyl)trifluoroacetamideHCID 76400Trichloroacetyl isocyanate2×HCID 20242418HCID 20242418, compound

Product 1

HCID 20242398HCID 20242398, compoundYield 89.6%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a mixture of 2-diphenylmethoxycarbonyl-3-oxothiomorpholine (327 mg, 1 mM), dichloromethane (8 ml), and bistrimethylsilyltrifluoroacetamide (0.53 ml). After 30 minutes' stirring from addition of trichloroacetyl isocyanate (0.18 ml), another trichloroacetyl isocyanate (0.06 ml) is added. After another 30 minutes' stirring, the mixture is concentrated and subjected to silica gel chromatography. Fractions eluted with dichloromethane and a mixture of dichloromethane and ethyl acetate (9:1) are combined and concentrated to give 2-diphenylmethoxycarbonyl-4-carbamoyl-3-oxothiomorpholine (332 mg). Yield 89.6%.

Workup

  1. concentrationthe mixture is concentrated
  2. washFractions eluted with dichloromethane
  3. additiona mixture of dichloromethane and ethyl acetate (9:1)
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-835ef3a5baf44ab3ae17494c898d4761
Source dataset
uspto-grants-1986_03
Patent number
US04578378

Reaction notes

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