Cyanamide → HCID 178424375, compound

HRID 1840364Notes

Reaction equation

HRID 1840364 reaction equation
[C:1](NC(N)=N)#[N:2].[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]=[C:15]=[N:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[C:10]([O:24][Si](C(C)(C)C)(C)C)[C:9]=1[S:32]([N:35]([CH3:37])[CH3:36])(=[O:34])=[O:33].[N:38]#CN.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>>[Cl:7][C:8]1[CH:13]=[CH:12][C:11]([N:14]([C:1]#[N:2])[C:15]([NH:16][C:17]2[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=2[CH3:23])=[NH:38])=[C:10]([OH:24])[C:9]=1[S:32]([N:35]([CH3:37])[CH3:36])(=[O:33])=[O:34]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 23447753HCID 23447753, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178424375HCID 178424375, compoundYield 32%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 12, N-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″,N″-dimethylaminosulfonyl)phenyl]-N′-(2-methylphenyl)carbodiimide (400 mg, 0.83 mmol), cyanamide (139.4 mg, 3.32 mmol) and N,N-diisopropylethylamine (129 mg, 1.0 mmol) were reacted, followed by desilylation with Cesium fluoride (152 mg, 1.0 mmol) to form the desired product (110 mg, 32%). EI-MS m/z 408.2 (M+). 1H NMR (DMSO-d6) δ 2.22 (s, 3H), 2.86 (s, 6H), 7.20 (m, 5H), 7.60 (d, 1H), 8.63(s, 1H), 8.96 (s, 1H), 10.50 (s, 1H).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-ea38c977c40a45938099d6cd8abe6e60
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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