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N,N-Diphenylcarbamic chloride → HCID 15550612, compound

HRID 1250093
Notes
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Reaction equation

HRID 1250093 reaction equation
[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][OH:13])[C:7]=1[Cl:14].C[Si]([N-][Si](C)(C)C)(C)C.[K+].[C:26]1([N:32]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[C:33](Cl)=[O:34])[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1>O1CCCC1>[CH3:1][O:2][C:3](=[O:15])[CH2:4][O:5][C:6]1[CH:11]=[CH:10][CH:9]=[C:8]([CH2:12][O:13][C:33](=[O:34])[N:32]([C:36]2[CH:37]=[CH:38][CH:39]=[CH:40][CH:41]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[C:7]=1[Cl:14]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 65741N,N-Diphenylcarbamic chlorideHCID 3251421Potassium bis(trimethylsilyl)amideHCID 15550611Methyl 2-[2-chloro-3-(hydroxymethyl)phenoxy]acetate

Product 1

HCID 15550612HCID 15550612, compoundYield 48%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Conditions

Temperature
-78 °C

Procedure

A solution of (2-chloro-3-hydroxymethylphenoxy)acetic acid methyl ester (1.94 g, 8.41 mmol) in tetrahydrofuran was cooled to −78° C., treated with potassium bis(trimethylsilyl)amide (10.1 mmol), and allowed to stir at −78° C. for about an hour. A solution of diphenylcarbamyl chloride (2.92 g, 12.6 mmol) in tetrahydrofuran was added dropwise, and the resulting mixture was allowed to warm to room temperature and stirred overnight. The mixture was quenched with water, diluted with diethyl ether, and the layers were separated. The aqueous layer was extracted twice more with diethyl ether. The combined organic extracts were dried over sodium sulfate and concentrated in vacuo. Purification of the residue by silica gel flash chromatography, eluting with hexane/acetone (4:1), gave {2-chloro-3-[(diphenyl-carbamoyloxy)methyl]phenoxy}acetic acid methyl ester as a white crystalline solid (1.72g, 48.0%).

Workup

  1. temperatureto warm to room temperature
  2. stirringstirred overnight
  3. customThe mixture was quenched with water
  4. additiondiluted with diethyl ether
  5. customthe layers were separated
  6. extractionThe aqueous layer was extracted twice more with diethyl ether
  7. dry with materialThe combined organic extracts were dried over sodium sulfate
  8. concentrationconcentrated in vacuo
  9. customPurification of the residue by silica gel flash chromatography
  10. washeluting with hexane/acetone (4:1)

Sources & evidence

ORD record
ord-cf543492742e40a59571c1f389a36a4e
Source dataset
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06335459B1

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes