Cyanamide → HCID 178455105, compound

HRID 1840350Notes

Reaction equation

[C:1](NC(N)=N)#[N:2].[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[N:15]=[C:16]=[N:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([S:25]([NH:28][CH:29]2[CH2:33][CH2:32][O:31][NH:30]2)(=[O:27])=[O:26])[C:19]=1[O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:37])[CH3:36].[N:42]#CN.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>>[Cl:7][C:8]1[C:13]([Cl:14])=[CH:12][CH:11]=[CH:10][C:9]=1[N:15]([C:1]#[N:2])[C:16]([NH:17][C:18]1[CH:23]=[CH:22][C:21]([Cl:24])=[C:20]([S:25]([NH:28][CH:29]2[CH2:33][CH2:32][O:31][NH:30]2)(=[O:27])=[O:26])[C:19]=1[O:34][Si:35]([C:38]([CH3:41])([CH3:40])[CH3:39])([CH3:36])[CH3:37])=[NH:42]

Participants

Reactant 5

HCID 9864Cyanamide

HCID 25953Cesium fluoride

HCID 81531Diisopropylethylamine

HCID 131724303HCID 131724303, compound

HCID 178418324HCID 178418324, compound

Product 1

HCID 178455105HCID 178455105, compoundYield 40%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 1, N-(2,3-dichlorophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]carbodiimide (547 mg, 0.95 mmol), cyanamide (159 mg, 3.8 mmol) and N,N-diisopropylethylamine (150 mg, 1.14 mmol) were reacted, followed by desilylation with Cesium fluoride (174 mg, 1.14 mmol) to form the desired product (190 mg, 40%). LC-MS m/z 504.

Workup

customwere reacted

Sources & evidence

ORD record: ord-8b7ee7f6d67e4d6bae9c25e441ca3860
Source dataset: uspto-grants-2004_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06680317B2

Reaction notes

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