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Carbamic acid, ethyl ester → Ethyl di(4-docosoxyphenyl)methylcarbamate

HRID 1025056
Notes
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Reaction equation

HRID 1025056 reaction equation
[CH2:1]([O:23][C:24]1[CH:29]=[CH:28][C:27]([CH:30]([C:32]2[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[CH:34][CH:33]=2)O)=[CH:26][CH:25]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22].[C:61](=[O:66])([O:63][CH2:64][CH3:65])[NH2:62].CS(O)(=O)=O.C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[CH2:64]([O:63][C:61](=[O:66])[NH:62][CH:30]([C:32]1[CH:37]=[CH:36][C:35]([O:38][CH2:39][CH2:40][CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH2:48][CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH2:56][CH2:57][CH2:58][CH2:59][CH3:60])=[CH:34][CH:33]=1)[C:27]1[CH:28]=[CH:29][C:24]([O:23][CH2:1][CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH2:10][CH2:11][CH2:12][CH2:13][CH2:14][CH2:15][CH2:16][CH2:17][CH2:18][CH2:19][CH2:20][CH2:21][CH3:22])=[CH:25][CH:26]=1)[CH3:65]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 5641Carbamic acid, ethyl esterHCID 6395Methanesulfonic Acid2×HCID 10340Sodium CarbonateHCID 469361424,4'-Didocosoxybenzhydrol

Product 1

HCID 86646200Ethyl di(4-docosoxyphenyl)methylcarbamateYield 103.8%

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent

Conditions

Temperature
110 °C

Procedure

To bis-(4-docosoxy-phenyl)-methanol (28.5 g, 34.2 mmol) were added toluene (350 mL), ethyl carbamate (6.1 g, 68.5 mmol), and methanesulfonic acid (333 μL, 5.14 mmol), and the mixture was stirred at 110° C. for 2 hours. Methanesulfonic acid (333 μL, 5.14 mmol) was added, and the mixture was stirred for 30 minutes. After stirring, the reaction mixture was cooled to room temperature, sodium carbonate (1.1 g, 8.73 mmol) was added and the solvent was evaporated. The residue was crystallized from methanol (400 mL) to give ethyl[bis-(4-docosoxy-phenyl)-methyl]carbamate (32.1 g, 100%).

Workup

  1. stirringthe mixture was stirred for 30 minutes
  2. stirringAfter stirring
  3. temperaturethe reaction mixture was cooled to room temperature
  4. customthe solvent was evaporated
  5. customThe residue was crystallized from methanol (400 mL)

Sources & evidence

ORD record
ord-1f3e3192d2c84eca83fd2c9d958b5b72
Source dataset
uspto-grants-2014_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08722934B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes