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Sodium hydride → HCID 15614945, compound

HRID 620357
Notes
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Reaction equation

HRID 620357 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:17])([F:16])[F:15])[C:5]=1[C:20]([NH:22][C:23](=[O:26])[O:24][CH3:25])=[O:21].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>C1COCC1>[Br:3][C:4]1[CH:13]=[CH:12][C:11]2[C:6](=[CH:7][CH:8]=[C:9]([O:18][CH3:19])[C:10]=2[C:14]([F:16])([F:17])[F:15])[C:5]=1[C:20]([N:22]([C:23]([O:24][CH3:25])=[O:26])[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30])=[O:21]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 79177tert-Butyl bromoacetateHCID 15614951HCID 15614951, compound

Product 1

HCID 15614945HCID 15614945, compoundYield 84%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
60 °C

Procedure

Sodium hydride (2.61 g, 6.43 mmol) was added to a stirred solution of N-[[2-bromo-6-methoxy-5-(trifluoromethyl)-1-naphthalenyl]carbonyl]carbamic acid, methyl ester (2.61 g, 6.43 mmol) in dry THF (95 mL) at room temperature under a dry N2 atmosphere. After 1 hour, tert-butyl bromoacetate (1.56 mL, 1.5 eq) was added and the reaction mixture was heated at 60° C. for 2.5 hours. The reaction mixture was cooled to room temperature and the THF was removed. Water (100 mL) was added and the resulting solid was filtered. The resulting solid was washed with water and then petroleum ether and dried in vacuo to provide the title compound as a white solid (2.81 g, 84%). A small portion was recrystallized from petroleum ether:ether, m.p. 126°-128° C.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customthe THF was removed
  3. additionWater (100 mL) was added
  4. filtrationthe resulting solid was filtered
  5. washThe resulting solid was washed with water
  6. dry with materialpetroleum ether and dried in vacuo

Sources & evidence

ORD record
ord-2eb977371e2947cda6a3caab0a1f7fcb
Source dataset
uspto-grants-1989_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04820727

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes