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Sodium Carbonate → Phenyl [2-(phenylthio)phenyl]carbamate

HRID 1638286
Notes
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Reaction equation

HRID 1638286 reaction equation
[CH:1]1[CH:6]=[CH:5][C:4]([S:7][C:8]2[C:13]([NH2:14])=[CH:12][CH:11]=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.Cl[C:16]([O:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:17].[OH-].[Na+].C(=O)([O-])[O-].[Na+].[Na+]>C1(C)C=CC=CC=1>[C:4]1([S:7][C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:13]=2[NH:14][C:16](=[O:17])[O:18][C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)[CH:5]=[CH:6][CH:1]=[CH:2][CH:3]=1
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 14798Sodium HydroxideHCID 15891Phenyl chloroformate2×HCID 3653932-(Phenylthio)aniline

Product 1

HCID 11209446Phenyl [2-(phenylthio)phenyl]carbamate

Reagents, catalysts & solvents 1

HCID 1140
Toluene
Solvent
3×

Conditions

Temperature
5 °C

Procedure

2-Amino diphenylsulfide (0.4 mole) was dissolved in toluene (500 ml) and cooled to 5° C. Phenyl chloroformate (0.24 mole) in toluene (50 ml) was added slowly to the stirred solution over 1 hour. When addition was complete a simultaneous addition of phenyl chloroformate (0.24 mole) in toluene (50 ml) and an aqueous solution of sodium hydroxide (0.3 mole) and sodium carbonate (0.35 mole) (200 ml) was started.

Workup

  1. additionWhen addition

Sources & evidence

ORD record
ord-5636952afe684bcfa10cbbd4256351ea
Source dataset
uspto-grants-1989_11
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04879288

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes