tert-Butanol → 1,1-Dimethylethyl N-(4-chloro-2-nitrophenyl)carbamate

HRID 498168Notes

Reaction equation

HRID 498168 reaction equation
[N-]=[C:2]=[O:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([NH2:11])=[C:7]([N+:12]([O-:14])=[O:13])[CH:6]=1.O=C(Cl)OC(Cl)(Cl)Cl.[C:23]([OH:27])([CH3:26])([CH3:25])[CH3:24]>CCOC(C)=O.C(Cl)Cl>[C:23]([O:27][C:2](=[O:3])[NH:11][C:8]1[CH:9]=[CH:10][C:5]([Cl:4])=[CH:6][C:7]=1[N+:12]([O-:14])=[O:13])([CH3:26])([CH3:25])[CH3:24]

Participants

7

Reactant 4

HCID 6386tert-ButanolHCID 69794-Chloro-2-nitroanilineHCID 10426DiphosgeneHCID 105034Isocyanate

Product 1

HCID 539801451,1-Dimethylethyl N-(4-chloro-2-nitrophenyl)carbamate

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

The title compound was prepared via the isocyanate from commercially available 4-chloro-2-nitro-phenylamine [CAS-No. 89-63-4] (5.0 g, 29 mmol) with diphosgene (1.75 mL, 14.5 mmol) in EtOAc (60 mL), followed by treatment with tert-BuOH (30 mL) in CH2Cl2 (60 mL) according to the general procedure A (method a). Obtained as a yellow solid (6.2 g, 76%).

Sources & evidence

ORD record
ord-4f06c740e5634043a74bf44a87746c3f
Source dataset
uspto-grants-2005_09
Patent number
US06949542B2

Reaction notes

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