Cyanamide → HCID 178486153, compound

HRID 1840355Notes

Reaction equation

HRID 1840355 reaction equation
[C:1](NC(N)=N)#[N:2].[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]=[C:15]=[N:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([S:24]([N:27]([CH3:29])[CH3:28])(=[O:26])=[O:25])[C:18]=1O[Si](C(C)(C)C)(C)C.[N:38]#CN.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>>[Cl:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][C:9]=1[N:14]([C:1]#[N:2])[C:15]([NH:16][C:17]1[CH:22]=[CH:21][C:20]([Cl:23])=[C:19]([S:24]([N:27]([CH3:28])[CH3:29])(=[O:25])=[O:26])[CH:18]=1)=[NH:38]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447743HCID 23447743, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178486153HCID 178486153, compoundYield 50%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 12, N-(2-chlorophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]carbodiimide (300 mg, 0.6 mmol), cyanamide (100 mg, 2.4 mmol) and N,N-diisopropylethylamine (94 mg, 0.72 mmol) were reacted, followed by desilylation with Cesium fluoride (110 mg, 0.72 mmol) to form the desired product (129 mg, 50%). EI-MS m/z 428.0 (M+). 1H NMR (DMSO-d6) δ 2.86 (s, 6H), 7.2 (d, 1H), 7.32 (t, 1H), 7.36 (t, 1H), 7.43 (d, 1H), 7.51 (d, 1H), 7.57 (d, 1H), 8.98 (s, 1H), 9.18 (s, 1H), 10.51 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-5c6dc53bff9e421c88e3580a906c461a
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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