Ammonia → tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamate

HRID 875140Notes

Reaction equation

HRID 875140 reaction equation
[C:1]([O:5][C:6]([NH:8][C:9](=[N:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])SC)=[O:7])([CH3:4])([CH3:3])[CH3:2].[NH3:20]>CO>[C:1]([O:5][C:6]([NH:8][C:9]([NH:12][C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])=[NH:20])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 222AmmoniaHCID 5466031,3-DI-Boc-2-methylisothiourea

Product 1

HCID 135638421tert-butyl N-({[(tert-butoxy)carbonyl]amino}methanimidoyl)carbamateYield 74%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

15 g of 1,3-bis(tert-butoxycarbonyl)-2-methyl-2-thiopseudourea (0.052 mol) were suspended in 150 mL of gaseous ammonia in methanol and the mixture was stirred at room temperature in a close bottle at room temperature. The resulting solution was concentrated in vacuo until 10 g (74% yield) of the title compound precipitated which were collected by filtration.

Sources & evidence

ORD record
ord-833a18107d6e48acab273755acf16f43
Source dataset
uspto-grants-2015_03
Patent number
US08981089B2

Reaction notes

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