2,3-Diaminotoluene → HCID 86712415, compound

HRID 404991Notes

Reaction equation

HRID 404991 reaction equation
N[C:2]1[C:3]([NH2:9])=[C:4]([CH3:8])[CH:5]=[CH:6][CH:7]=1.[C:10](=[O:24])([O:12]C1C=[C:18]([O:20][C:21](=[O:23])[NH2:22])[CH:17]=[CH:16][C:14]=1C)[NH2:11]>>[CH3:8][C:4]1[CH:5]=[CH:6][C:7]([NH:11][C:10](=[O:12])[OH:24])=[CH:2][C:3]=1[NH:9][C:10](=[O:12])[OH:24].[CH2:18]([O:20][C:21]([NH:9][C:3]1[CH:2]=[C:7]([NH:22][C:21]([O:20][CH2:18][CH2:17][CH2:16][CH3:14])=[O:23])[CH:6]=[CH:5][C:4]=1[CH3:8])=[O:23])[CH2:17][CH2:16][CH3:14].[CH3:8][C:4]1[C:5]([NH:11][C:10](=[O:12])[OH:24])=[CH:6][CH:7]=[CH:2][C:3]=1[NH:9][C:10](=[O:12])[OH:24].[CH2:18]([O:20][C:21]([NH:22][C:5]1[CH:6]=[CH:7][CH:2]=[C:3]([NH:9][C:21]([O:20][CH2:18][CH2:17][CH2:16][CH3:14])=[O:23])[C:4]=1[CH3:8])=[O:23])[CH2:17][CH2:16][CH3:14]

Participants

4

Reactant 2

HCID 175932,3-Diaminotoluene2×HCID 14008947HCID 14008947, compound

Product 2

HCID 86712415HCID 86712415, compoundHCID 86712416HCID 86712416, compound

Procedure

Tolylene dicarbamate was obtained in the same manner as in Example 1, except that the reaction time in the carbamate-forming reaction was set to 10 hours and that 8 g of the decomposed diaminotoluene (second diaminotoluene) obtained in Preparation Example 2 was blended with 100 g of the first diaminotoluene in the mixing step. It was confirmed that tolylene dicarbamate was obtained at a yield of 98 mol % as the total amount of 2,4-bis(butoxycarbonylamino)toluene (2,4-tolylene dicarbamate) and 2,6-bis(butoxycarbonylamino)toluene (2,6-tolylene dicarbamate). The isomer ratio of the mixed diaminotoluene was 2,4-diaminotoluene/2,6-diaminotoluene=81.1/18.9 (molar ratio).

Workup

  1. customforming
  2. customreaction

Sources & evidence

ORD record
ord-734cf274ce8642c98829cdbbffece3a9
Source dataset
uspto-grants-2014_06
Patent number
US08748654B2

Reaction notes

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