Cyanamide → HCID 178455104, compound

HRID 1840349Notes

Reaction equation

HRID 1840349 reaction equation
[C:1](NC(N)=N)#[N:2].[Br: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]([NH:27][CH:28]2[CH2:32][CH2:31][O:30][NH:29]2)(=[O:26])=[O:25])[C:18]=1[O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:36])[CH3:35].[N:41]#CN.C(N(CC)C(C)C)(C)C.[F-].[Cs+]>>[Br: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]([NH:27][CH:28]2[CH2:32][CH2:31][O:30][NH:29]2)(=[O:26])=[O:25])[C:18]=1[O:33][Si:34]([C:37]([CH3:40])([CH3:39])[CH3:38])([CH3:35])[CH3:36])=[NH:41]

Participants

6

Reactant 5

HCID 9864CyanamideHCID 25953Cesium fluorideHCID 81531DiisopropylethylamineHCID 131724302HCID 131724302, compoundHCID 178418324HCID 178418324, compound

Product 1

HCID 178455104HCID 178455104, compoundYield 26%

Procedure

Following the general procedure for cyanoguanidine formation outlined in example 1, N-(2-bromophenyl)-N′-[4-chloro-2-tert-butyldimethylsilyloxy-3-(N″-tetrahydroisoxazylaminosulfonyl)phenyl]carbodiimide (385 mg, 0.79 mmol), cyanamide (133 mg, 3.16 mmol) and N,N-diisopropylethylamine (127 mg, 0.95 mmol) were reacted, followed by desilylation with Cesium fluoride (144 mg, 0.95 mmol) to form the desired product (100 mg, 26%). EI-MS m/z 515 (M+).

Workup

  1. customwere reacted

Sources & evidence

ORD record
ord-74c8a00846aa493abbff3af45142a88a
Source dataset
uspto-grants-2004_01
Patent number
US06680317B2

Reaction notes

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